Potassium Carbonate → HCID 12083573, compound

HRID 1357272Notes

Reaction equation

HRID 1357272 reaction equation
[Br:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:13][N:14]([CH3:31])[C:15]([C:17]1[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH3:26])[C:18]=1[CH2:27][CH2:28][CH2:29][CH3:30])=[O:16])=[CH:7]2.Br[CH2:33][C:34]#[N:35].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:11]([O:12][CH2:33][C:34]#[N:35])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:13][N:14]([CH3:31])[C:15]([C:17]1[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH3:26])[C:18]=1[CH2:27][CH2:28][CH2:29][CH3:30])=[O:16])=[CH:7]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 86587389HCID 86587389, compound

Product 1

HCID 12083573HCID 12083573, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-butyl-1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (2.09 g, 4.36 mmol), prepared in the previous step, bromoacetonitrile (364 μL, 5.23 mmol) and potassium carbonate (3.01 g, 21.8 mmol) in 50 mL of DMF was stirred under nitrogen at room temperature for 16 h (overnight). The reaction was partitioned between ethyl acetate and water. The organic layer was separated, extracted multiple times with water, dried (MgSO4) and the solvent removed under reduced pressure to give 2-butyl-1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (2.00 g, 88%) as a brown solid foam, MS m/z: 518 [M+H]+.

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. extractionextracted multiple times with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b4fddcb6f7e2467986f51de1e107675c
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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