Methanol → 6-Amino-4-(3-bromoanilino)[1]benzothieno[3,2-b]pyridine-3-carbonitrile

HRID 2213769Notes

Reaction equation

HRID 2213769 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[NH:5][C:6]1[C:11]([C:12]#[N:13])=[CH:10][N:9]=[C:8]2[C:14]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[C:15]=3[S:16][C:7]=12.CO>[Fe].O>[NH2:21][C:17]1[C:15]2[S:16][C:7]3[C:8](=[N:9][CH:10]=[C:11]([C:12]#[N:13])[C:6]=3[NH:5][C:4]3[CH:24]=[CH:25][CH:26]=[C:2]([Br:1])[CH:3]=3)[C:14]=2[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 219564224-(3-Bromoanilino)-6-nitro[1]benzothieno[3,2-b]pyridine-3-carbonitrile

Product 1

HCID 219564126-Amino-4-(3-bromoanilino)[1]benzothieno[3,2-b]pyridine-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 4-(3-bromoanilino)-6-nitro[1]benzothieno[3,2-b]pyridine-3-carbonitrile (0.213 g, 0.5 mmol), iron powder (0.168 g, 3.0 mmol) ammonium chloride (0.325 g, 6.0 mmol), methanol (90 mL) and water (90 mL) is heated at reflux temperature with vigorous stirring under nitrogen for 12 hours. The final mixture is concentrated, and the residue is extracted with ethyl acetate (5×20 mL). The extract is dried over sodium sulfate, evaporated, and re-dissolved in a small volume of chloroform/methanol/DMSO. Purification by silica gel chromatography, eluting with 20:1 chloroform/methanol, yields 6-amino-4-(3-bromoanilino)[1]benzothieno[3,2-b]pyridine-3-carbonitrile as a brown solid, m.p. 256–258° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature
  3. concentrationThe final mixture is concentrated
  4. extractionthe residue is extracted with ethyl acetate (5×20 mL)
  5. dry with materialThe extract is dried over sodium sulfate
  6. customevaporated
  7. dissolutionre-dissolved in a small volume of chloroform/methanol/DMSO
  8. customPurification by silica gel chromatography
  9. washeluting with 20:1 chloroform/methanol

Sources & evidence

ORD record
ord-7657938c42d44c049b4b26903dd834e8
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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