2-Isopropyl-5-methyl-cyclohexanecarboylic acid [2-(2-bromo-phenyl)-ethyl]-amide → 2-Isopropyl-5-methyl-cyclohexanecarboxylic acid [2-(2-cyano-phenyl)-ethyl]-amide

HRID 501472Notes

Reaction equation

HRID 501472 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][C:11]([CH:13]1[CH2:18][CH:17]([CH3:19])[CH2:16][CH2:15][CH:14]1[CH:20]([CH3:22])[CH3:21])=[O:12].[C:23]([Cu])#[N:24]>CN1C(=O)CCC1>[C:23]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][C:11]([CH:13]1[CH2:18][CH:17]([CH3:19])[CH2:16][CH2:15][CH:14]1[CH:20]([CH3:22])[CH3:21])=[O:12])#[N:24]

Participants

4

Reactant 2

HCID 668315152-Isopropyl-5-methyl-cyclohexanecarboylic acid [2-(2-bromo-phenyl)-ethyl]-amideHCID 178418546HCID 178418546, compound

Product 1

HCID 668315242-Isopropyl-5-methyl-cyclohexanecarboxylic acid [2-(2-cyano-phenyl)-ethyl]-amideYield 95.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A 20 mL microwave reaction vessel equipped with a stir bar was charged with 2-isopropyl-5-methyl-cyclohexanecarboylic acid [2-(2-bromo-phenyl)-ethyl]-amide (1.54 g, 4.2 mmol), CuCN (0.60 g, 6.4 mmol) and NMP (10 mL). The reaction vessel was subjected to microwave at 180° C. for 40 minutes. The reaction mixture was transferred to a round bottom flask and concentrated. The residue to purified by flash chromatography on silica gel (10% ethyl acetate/hexane for elution) to give a colorless solid (1.25 g, 81%).

Workup

  1. customA 20 mL microwave reaction vessel equipped with a stir bar
  2. customThe reaction mixture was transferred to a round bottom flask
  3. concentrationconcentrated
  4. customThe residue to purified by flash chromatography on silica gel (10% ethyl acetate/hexane for elution)

Sources & evidence

ORD record
ord-3f89db5cf5204077aeaf15de31ee037c
Source dataset
uspto-grants-2010_08
Patent number
US07772266B2

Reaction notes

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