Ammonia → 5-Benzyloxy-6-methyl-1H-indole-2-carboxylic acid methyl ester

HRID 1258187Notes

Reaction equation

HRID 1258187 reaction equation
[CH3:1][O:2][C:3](=[O:33])/[C:4](/OCC1C=CC=CC=1)=[C:5](/N=C=O)\[C:6]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]([CH3:20])=[CH:8][C:7]=1Br.C([O-])(=O)C.[Cs+].[NH3:39]>CS(C)=O.[Cu]I>[CH3:1][O:2][C:3]([C:4]1[NH:39][C:7]2[C:6]([CH:5]=1)=[CH:11][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[C:9]([CH3:20])[CH:8]=2)=[O:33]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 5152919Cesium acetateHCID 86657627(Z)-3-(5-benzyloxy-2-bromo-4-methylphenyl)-2-benzyloxy-carbonylaminoacrylic acid methyl ester

Product 1

HCID 584374865-Benzyloxy-6-methyl-1H-indole-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (Z)-3-(5-benzyloxy-2-bromo-4-methylphenyl)-2-benzyloxy-carbonylaminoacrylic acid methyl ester (0.2 g) and copper (I) iodide (0.075 g) in dimethylsulfoxide (8 mL) was added cesium acetate (0.38 g) at room temperature and this mixture was stirred under argon atmosphere at 90° C. for 5 hours. To this reaction mixture was added aqueous ammonia solution (28%) and the precipitated solid was collected by filtration, and washed with water, dried under reduced pressure to give the title compound (0.073 g).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-195a60ee40e64c0ea3151fd016263c1d
Source dataset
uspto-grants-2013_06
Patent number
US08466152B2

Reaction notes

Loading…