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

HRID 73330Notes

Reaction equation

HRID 73330 reaction equation
[CH3:1][O:2][C:3](=[O:33])/[C:4](/[NH:22]C(OCC1C=CC=CC=1)=O)=[CH:5]/[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+].N>CS(C)=O.[Cu]I>[CH3:1][O:2][C:3]([C:4]1[NH:22][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 58437218(Z)-3-(5-benzyloxy-2-bromo-4-methylphenyl)-2-benzyloxycarbonylaminoacrylic acid methyl ester

Product 1

HCID 584374865-Benzyloxy-6-methyl-1H-indole-2-carboxylic acid methyl esterYield 63.1%

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-benzyloxycarbonylaminoacrylic 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-865e985d28cb44e48a972d7c9f48d8fb
Source dataset
uspto-grants-2014_09
Patent number
US08829040B2

Reaction notes

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