Methyl 2-(bromomethyl)-6-methylbenzoate → ethyl 2-(6-(7-methyl-1-oxoisoindolin-2-yl)-1H-indol-1-yl)acetate

HRID 453863Notes

Reaction equation

HRID 453863 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1.Br[CH2:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:20]=1[C:21](OC)=[O:22]>C1C=CC=CC=1.ClCCl>[CH3:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[C:21](=[O:22])[N:1]([C:2]1[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][N:8]3[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1)[CH2:29]2

Participants

5

Reactant 2

HCID 10263795Methyl 2-(bromomethyl)-6-methylbenzoateHCID 16731704Ethyl 2-(6-amino-1H-indol-1-yl)acetate2×

Product 1

HCID 59473657ethyl 2-(6-(7-methyl-1-oxoisoindolin-2-yl)-1H-indol-1-yl)acetateYield 64%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-(6-amino-1H-indol-1-yl)acetate (intermediate B) (7.66 mmol, 1 equiv.) was dissolved in benzene (30 ml), and methyl 2-(bromo-methyl)-6-methylbenzoate (8.42 mol, 1.1 equiv.) and TEA (9.19 mmol, 1.2 equiv.) were added at 25° C. and the mixture was refluxed for 12 h. The reaction mixture was reduced under reduced pressure and the residue was taken up in dichloromethane (30 ml), washed with water and sat. NaCl solution (5 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (10% ethyl acetate in hexane). Yield: 64%

Workup

  1. temperaturethe mixture was refluxed for 12 h
  2. washwashed with water and sat. NaCl solution (5 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-15f20744fb304cf4ba7654645aa3c242
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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