Potassium Carbonate → 1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide

HRID 1357277Notes

Reaction equation

HRID 1357277 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]([CH3:27])[C:15]([C:17]1[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH3:26])[CH:18]=1)=[O:16])=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][C:36]#[N:37]>CN(C=O)C>[Br:1][C:2]1[C:11]([O:12][CH2:35][C:36]#[N:37])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:13][N:14]([CH3:27])[C:15]([C:17]1[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH3:26])[CH:18]=1)=[O:16])=[CH:7]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 865873931-methyl-1H-indole-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide

Product 1

HCID 120835741-methyl-1H-indole-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amideYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (2.0 g, 4.72 mmol), prepared in the previous step, potassium carbonate (3.26 g, 23.6 mmol) and bromoacetonitrile (0.39 mL, 5.67 mmol) in 60 mL of DMF was stirred under nitrogen at room temperature for 24 h (overnight). The reaction was partitioned between ethyl acetate and water. The organic layer was separated, extracted five times with water, dried (MgSO4) and the solvent removed under reduced pressure to give 1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (2.06 g, 94.5%) as a tan solid, mp 148-150° C.

Workup

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

Sources & evidence

ORD record
ord-19b2618e7db24f3e8238c3d0bc8937c6
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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