Borane → HCID 21254087, compound

HRID 1531546Notes

Reaction equation

HRID 1531546 reaction equation
[CH2:1]([N:8]([CH2:33][CH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([NH:43][S:44]([CH3:47])(=[O:46])=[O:45])=[CH:39][CH:38]=1)[C:9](=O)[C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=2)[NH:14][C:13]=1[C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[CH:25]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B>O1CCCC1>[CH2:1]([N:8]([CH2:9][CH2:10][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=2)[NH:14][C:13]=1[C:24]1[CH:25]=[C:26]([CH3:31])[CH:27]=[C:28]([CH3:30])[CH:29]=1)[CH2:33][CH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([NH:43][S:44]([CH3:47])(=[O:46])=[O:45])=[CH:39][CH:38]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 21254044HCID 21254044, compound

Product 1

HCID 21254087HCID 21254087, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-benzyl-2-[2-(3,5-dimethylphenyl)-5-nitro-1H-indol-3-yl]-N-[4-(4-methanesulfonylaminophenyl)butyl]-2-oxo-acetamide (391 mg in 20 mL dry tetrahydrofuran) was added 5.5 mL of a 1M 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 (1.8 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 (hexane:ethyl acetate, 3:2) gave the title compound (317 mg).

Workup

  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 (1.8 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 (hexane:ethyl acetate, 3:2)

Sources & evidence

ORD record
ord-466008a9ac434bcb9e2ed6396431e87c
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

Loading…