3-Bromoaniline → 4-(3-Bromoanilino)-6-nitro[1]benzothieno[3,2-b]pyridine-3-carbonitrile

HRID 2213768Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[C:10]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[C:11]=3[S:12][C:3]=12.[Br:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24].Cl.N1C=CC=CC=1>CS(C)=O.C(Cl)(Cl)Cl>[Br:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH:24][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[C:10]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[C:11]=3[S:12][C:3]=12

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 4-chloro-6-nitro[1]benzothieno[3,2-b]pyridine-3-carbonitrile (0.27 g, 0.9 mmol), 3-bromoaniline (3.16 g, 18.4 mmol), and pyridine hydrochloride (0.06 g) in 15 mL of DMSO is stirred in the microwave (PROLABO unit) at 140° C., power range 0–10%, for one hour. The final reaction mixture is cooled, dissolved in 100 mL of chloroform, washed with 2N HCl (2×50 mL), then with saturated aqueous sodium bicarbonate (50 mL), and dried over sodium sulfate. The solvent is evaporated, and the desired compound purified by silica gel chromatography, eluting with 9:1 chloroform/methanol. After washing with diethyl ether and ethyl acetate, 4-(3-bromoanilino)-6-nitro[1]benzothieno[3,2-b]pyridine-3-carbonitrile (0.215 g, 55%) is obtained as a yellow solid, m.p. 288–290° C.

Workup

customThe final reaction mixture
temperatureis cooled
washwashed with 2N HCl (2×50 mL)
dry with materialwith saturated aqueous sodium bicarbonate (50 mL), and dried over sodium sulfate
customThe solvent is evaporated
customthe desired compound purified by silica gel chromatography
washeluting with 9:1 chloroform/methanol
washAfter washing with diethyl ether and ethyl acetate

Sources & evidence

ORD record: ord-b217132380424aa0b190b035bc060442
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105531B2

Reaction notes

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