Benzyl Bromide → HCID 86615523, compound

HRID 420817Notes

Reaction equation

HRID 420817 reaction equation
[CH:1]([C:4]1[NH:5][C:6]2[C:11]([C:12]=1[CH:13]=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2)([CH3:3])[CH3:2].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH2:15]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]([CH:13]=[O:14])=[C:4]1[CH:1]([CH3:3])[CH3:2])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 13383890HCID 13383890, compound2×

Product 1

HCID 86615523HCID 86615523, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-isopropyl-1H-indole-3-carbaldehyde (Compound 39, 1.19 g, 6.4 mmol) in DMF (6.0 ml) was added benzyl bromide (1.5 ml, 12.8 mmol) and K2CO3 (2.65 g, 19.2 mmol). The mixture was stirred at room temperature for 24 h and was diluted with EtOAc, washed with H2O, brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with 0-30% EtOAc-hexanes to yield 1-benzyl-2-isopropyl-1H-indole-3-carbaldehyde (Compound 40) as a light brown solid.

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel eluting with 0-30% EtOAc-hexanes

Sources & evidence

ORD record
ord-d5e35ff5c2ad49aa8a5d3b6dd41636c2
Source dataset
uspto-grants-2012_01
Patent number
US08097644B2

Reaction notes

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