4-(Methanesulfonyl)phenylboronic acid → 8-(4-Methanesulfonyl-phenyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

HRID 1970067Notes

Reaction equation

HRID 1970067 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[C:6]3[NH:13][CH:14]=[CH:15][C:5]=3[C:4]=2[CH:3]=1.[CH2:16]([C:18]([O-:20])=[O:19])[CH3:17].[CH3:21][S:22]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)(=[O:24])=[O:23]>>[CH3:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:11]=[CH:10][C:9]3[NH:8][C:7](=[O:12])[C:6]4[NH:13][CH:14]=[CH:15][C:5]=4[C:4]=3[CH:3]=2)=[CH:27][CH:26]=1)(=[O:24])=[O:23].[CH2:16]([C:18]([O-:20])=[O:19])[CH3:17]

Participants

3

Reactant 2

HCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 866275178-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Product 1

HCID 1317305268-(4-Methanesulfonyl-phenyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Procedure

This compound is prepared according to synthesis 229, from 200 mg (0.49 mmol) of 8-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate and 110 mg (0.55 mmol) of 4-methanesulfonylphenylboronic acid to give, after purification by chromatography on silica (eluent dichloromethane/methanol 95/5), 49 mg (32%) of 8-(4-methanesulfonyl-phenyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Workup

  1. customThis compound is prepared
  2. customto give
  3. customafter purification by chromatography on silica (eluent dichloromethane/methanol 95/5), 49 mg (32%) of 8-(4-methanesulfonyl-phenyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid

Sources & evidence

ORD record
ord-560c4109bb1b4d599112f4f222f0a652
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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