Water → HCID 57894455, compound

HRID 1822161Notes

Reaction equation

HRID 1822161 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=[O:15])[CH:12]([CH3:14])[CH3:13])=[CH:5]2.[OH-].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C>[CH2:18]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:11](=[O:15])[CH:12]([CH3:13])[CH3:14])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 57894437HCID 57894437, compound

Product 1

HCID 57894455HCID 57894455, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(5-chloro-1H-indole-2-yl)-2-methylpropan-1-one (1 mmol) in 15 mL of DMF, was added KOH (2 mmol) at 0° C. The mixture was stirred for 30 min., followed by adding benzyl bromide (2 mmol) slowly. The mixture was warmed up to room temperature and stirred for additional 1 h. The solution was poured into water, and extracted with EtOAc (×3). The organic layers were combined, washed with H2O (×3), brine (×3), dried (Na2SO4), filtered, and the filtrate was concentrated. The material was purified by flash chromatography (10% EtOAc:hexane) to yield 1-(1-benzyl-5-chloro-1H-indole-2-yl)-2-methylpropan-1-one.

Workup

  1. stirringstirred for additional 1 h
  2. extractionextracted with EtOAc (×3)
  3. washwashed with H2O (×3), brine (×3)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe material was purified by flash chromatography (10% EtOAc:hexane)

Sources & evidence

ORD record
ord-4c1c1dd8653e4a17a374dd6fdbfee28c
Source dataset
uspto-grants-2009_10
Patent number
US07608723B2

Reaction notes

Loading…