Category: 1978-39-8

Application of 1978-39-8,Some common heterocyclic compound, 1978-39-8, name is 5-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A solution of sodium nitrite (36 g, 0.51 mole) in water (50 mL) was slowly added to a solution of 5-fluoro-2-methoxy-phenylamine (61.5 g, 0.48 mol) in hydrochloric acid (20 % aqueous solution, 115 mL) at 0 C. After stirring for 10 minutes, a cooled (0 C) solution of acrolein (50 mL, 0.75 mol) in acetone (100 mL) containing calcium oxide (0.56 g, 0.010 mol) was added slowly to the reaction mixture. This was then followed by a solution of cuprous chloride (5 g, 0.05 mol) in acetone (100 mL) containing hydrochloric acid (20 % aqueous solution, 10 mL). The mixture was stirred at 0 to 30 C for 3 hours, and then extracted three times with dichloromethane (300 mL). The combined organic layers were washed with a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered, and evaporated to dryness to give a black viscous oil. The crude product was passed through a short silica column to give the crude product, which was used directly in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Fluoro-2-methoxyaniline, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CLEVELAND, Thomas; MAKINGS, Lewis R.; HAMILTON, Matthew; GROOTENHUIS, Peter D.J.; WO2005/26137; (2005); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 1978-39-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1978-39-8 as follows.

Example 1 (3) obtained in 2 – [[5-phenyl-4-(lH-pyrrol-1-yl)-4H-1,2,4-triazol-3-yl] thio] acetic acid (90 mg, 0.3mmol),1-hydroxybenzotriazole (40mg, 0.3mmol),1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (60 mg, 0.3 mmol)Of N, N-dimethylformamide (2 ml)Was added triethylamine (0.09ml, 0.6mmol)When the 5-fluoro-2-methoxy aniline (0.04ml, 0.36mmol)Was stirred for 16 hours at room temperature added.The reaction solution was extracted by adding aqueous sodium bicarbonate solution and ethyl acetate, and extracted twice further the aqueous layer with ethyl acetate. After acidification with 1N hydrochloric acid was added to the organic layer, extracted, extracted twice further the aqueous layer with ethyl acetate. The organic layer was washed with saturated brine, and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, the residue was purified by column (hexane: ethyl acetate = 1: 3-1: 5) to give to N-(5-fluoro-2-methoxyphenyl) -2 – [[5-phenyl to give-4- (lH-pyrrol-1-yl) -4H-1,2,4- triazol-3-yl] thio] acetamide (20mg, 16%) as a pale brown solid.

According to the analysis of related databases, 1978-39-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chiba Prefecture; Nakagawara, Akira; Hoshino, Tadatsugu; Nakamura, Yoko; (15 pag.)JP2015/117182; (2015); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 1978-39-8,Some common heterocyclic compound, 1978-39-8, name is 5-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of compound Al (400 rng, 0.53 mrnoi) and 5-fluoro-2-rnethoxyaniline (150,7mg, 1.07 mmoi) intoluene (10 rnL) was added Ti(O-i] r)4 (151.6 mg, 0.53 mmoi). Themixture was stirred at 120 C over night under N2. The mixture was quenched with [120 (50 rnL) and extracted with DCM (20 mL x 3). The combined organic layer was dried over potassium carbonate, filtered and concentrated. The residue was purified by silica gel column chromatography (DCMMeOH = 15/i) to afford the crude products 29-1 and 29-2 (320 mg) as a yellow solid. LC-MS: m/z 89.4 [M+I-[. To a solution of compounds 29-1 and 292 (310 ing, 0.35 rnrnol) in DCM (5 mL) was added DAST (56.2mg, 0.35 mmoi) at -78 C underN2. After stirred at -78 C for 2 h, the mixture was quenched with aqueous NaHCO3 and 1-120 and then extracted with DCM (30 rnL x 3. The combined organic layer was dried over potassium carbonate, filtered and concentrated. The residue was purified by prep-HPLC to afford compound 29 (53 rng, yield17.5%) as white solid. Partial ?HNMR (CDC13, 400 MHz): 6.756.7I (m, 2H). 6.64-6.59 (rn, 2H), 4.89 (s, IH), 4.76-4.72 (rn. 1H), 4.43 (d, J= 8.0 Hz, IH), 4.34-4.30 (rn, TH), 3.87 (s. 3H). 2.59-2.50 (m, 21-1), LG-MS: m/z 871.4 [M¡ÀH.

The synthetic route of 1978-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGRIMETIS, LLC; CALABRESE, Andrew; (110 pag.)WO2018/132288; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem