Borane → HCID 21249905, 화합물

HRID 1956525노트

반응식

HRID 1956525 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 21249905HCID 21249905, 화합물수율 91.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-938d0d4e48514815a21b87fc2ec85385
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05780437

반응 노트

불러오는 중…