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

HRID 2213768
Notes
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Reaction equation

HRID 2213768 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 115623-BromoanilineHCID 10176127Pyridinium chlorideHCID 21956414HCID 21956414, compound

Product 1

HCID 219564224-(3-Bromoanilino)-6-nitro[1]benzothieno[3,2-b]pyridine-3-carbonitrileYield 56.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent
HCID 6212
Chloroform
Solvent

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

  1. customThe final reaction mixture
  2. temperatureis cooled
  3. washwashed with 2N HCl (2×50 mL)
  4. dry with materialwith saturated aqueous sodium bicarbonate (50 mL), and dried over sodium sulfate
  5. customThe solvent is evaporated
  6. customthe desired compound purified by silica gel chromatography
  7. washeluting with 9:1 chloroform/methanol
  8. 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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