Acetaldehyde → HCID 69511653, compound

HRID 969667Notes

Reaction equation

HRID 969667 reaction equation
[CH3:1][C:2]1([CH3:23])[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:22])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N+:19]([O-:21])=[O:20])=[CH:8][CH:9]=2)[NH:4][CH2:3]1.[CH:24](=O)[CH3:25].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH2:24]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([NH:11][C:12](=[O:22])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N+:19]([O-:21])=[O:20])[CH:6]=2)[C:2]([CH3:23])([CH3:1])[CH2:3]1)[CH3:25]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69511218HCID 69511218, compound

Product 1

HCID 69511653HCID 69511653, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(3,3-Dimethyl-2,3-dihydro-1H-indol-6-yl)-2-nitro-benzamide (Step B) (300 mg, 0.96 mmol) was treated with acetaldehyde (70 μL) and NaBH(OAc)3 (300 mg, 1.4 mmol) in CH2Cl2 (50 mL) overnight. After drying in vacuo, the reaction mixture was purified via flash chromatography on silica gel using EtOAc to afford the desired compound.

Workup

  1. customAfter drying in vacuo
  2. customthe reaction mixture was purified via flash chromatography on silica gel

Sources & evidence

ORD record
ord-bdf49a377c724603b4e705472e31ffab
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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