Sodium borohydride → HCID 90037884, compound

HRID 1055404Notes

Reaction equation

HRID 1055404 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[N:5]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:6]2[C:11]([C:12]=1[CH:13]=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2>C(Cl)Cl.CO.[NH4+].[Cl-].CCOC(C)=O>[Cl:3][C:4]1[N:5]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:16])=[O:17])[C:6]2[C:11]([C:12]=1[CH2:13][OH:14])=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 11109986HCID 11109986, compound

Product 1

HCID 90037884HCID 90037884, compoundYield 99.6%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

NaBH4 (7.81 mg, 0.206 mmol) was added to a solution of 2-chloro-1-(phenylsulfonyl)-1H-indole-3-carbaldehyde (33 mg, 0.103 mmol) in DCM/MeOH 1:1 (10 mL). After 16 h the mixture was diluted with sat. NH4Cl and EtOAc, the organic layer separated and washed with H2O, dried over MgSO4, filtered and the filtrate concentrated to give the title compound (33 mg, 99%) which was used without purification.

Workup

  1. customthe organic layer separated
  2. washwashed with H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-2df137619d9b497e8af44ddf93320e1c
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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