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

HRID 989328ノート

反応式

HRID 989328 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b1f9f338ee9e4297b005414fa6f62e79
出典データセット
uspto-grants-2003_10
特許番号
US06638929B2

反応ノート

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