Cesium carbonate → 2-(4-(3-chlorobenzyloxy)-5-fluoro-1-methyl-1H-indol-3-yl)-N-methyl acetamide

HRID 1404139Notes

Reaction equation

HRID 1404139 reaction equation
[F:1][C:2]1[C:3]([OH:17])=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[CH2:12][C:13]([NH:15][CH3:16])=[O:14].Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Cl:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[CH2:19][O:17][C:3]1[C:2]([F:1])=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH2:12][C:13]([NH:15][CH3:16])=[O:14])=[CH:6][N:7]2[CH3:11]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 583040072-(5-fluoro-4-hydroxy-1-methyl-1H-indol-3-yl)-N-methylacetamide

Product 1

HCID 583039872-(4-(3-chlorobenzyloxy)-5-fluoro-1-methyl-1H-indol-3-yl)-N-methyl acetamideYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 33-6 (40 mg, 0.17 mmol), 1-(bromomethyl)-3-chlorobenzene (35 mg, 0.17 mmol) and Cesium carbonate (166 mg, 0.51 mmol) in acetonitrile (20 mL) was refluxed for 2 h. After cooled to room temperature, the mixture was filtered and the filtrate was evaporated under vacuum. The resulting residue was purified by Preparative TLC (petroleum ether/ethyl acetate=1:3) to give 33-7 (50 mg, 82%) as a white solid. LRMS: calc 360.1 and found: 361.1 [M+1].

Workup

  1. temperaturewas refluxed for 2 h
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated under vacuum
  4. customThe resulting residue was purified by Preparative TLC (petroleum ether/ethyl acetate=1:3)

Sources & evidence

ORD record
ord-6bba1bcb2d674554b66b5cc5b8cb522b
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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