Borane → HCID 21249905、化合物

HRID 1956525ノート

反応式

HRID 1956525 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH:20][C:21](=O)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:15][C:14]([N+:29]([O-:31])=[O:30])=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.B>O1CCCC1>[CH2:21]([NH:20][CH2:19][CH2:18][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:29]([O-:31])=[O:30])[CH:15]=2)[NH:10][C:9]=1[C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[CH:3]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

4

反応物 2

HCID 6331BoraneHCID 21249902N-{2-[2-(3,5-dimethylphenyl)-5-nitro-1H-indol-3-yl]ethyl}benzamide

生成物 1

HCID 21249905HCID 21249905、化合物収率 91.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of N-{2-[2-(3,5-dimethylphenyl)-5-nitro-1H-indol-3-yl]ethyl}benzamide (1.7 g in 130 mL dry tetrahydrofuran) was added 35 mL of a IM solution of borane in tetrahydrofuran and the mixture heated slowly to reflux on an oil bath. After 2 hours the mixture was cooled to room temperature and the excess borane quenched by the careful addition of methanol. The mixture was concentrated to half-volume, treated with N,N-dimethylethanolamine (13 mL) and heated to reflux on an oil bath. After 3 hours the mixture was cooled to room temperature and concentrated in vacuo. Purification by flash chromatography on silica gel (methylene chloride:methanol, 97:3) gave the title compound (1.5 g).

後処理

  1. temperaturethe mixture heated slowly
  2. temperatureto reflux on an oil bath
  3. customthe excess borane quenched by the careful addition of methanol
  4. concentrationThe mixture was concentrated to half-volume
  5. additiontreated with N,N-dimethylethanolamine (13 mL)
  6. temperatureheated
  7. temperatureto reflux on an oil bath
  8. temperatureAfter 3 hours the mixture was cooled to room temperature
  9. concentrationconcentrated in vacuo
  10. customPurification by flash chromatography on silica gel (methylene chloride:methanol, 97:3)

出典と根拠

ORDレコード
ord-938d0d4e48514815a21b87fc2ec85385
出典データセット
uspto-grants-1998_07
特許番号
US05780437

反応ノート

読み込み中…