4-Cyanophenylboronic acid → HCID 131730527, compound

HRID 1970068Notes

Reaction equation

HRID 1970068 reaction equation
I[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].[C:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)#[N:22]>>[C:21]([C:23]1[CH:28]=[CH:27][C:26]([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:25][CH:24]=1)#[N:22].[CH2:16]([C:18]([O-:20])=[O:19])[CH3:17]

Participants

3

Reactant 2

HCID 27343264-Cyanophenylboronic acidHCID 86627515HCID 86627515, compound

Product 1

HCID 131730527HCID 131730527, compound

Procedure

This compound is prepared according to synthesis 229, from 200 mg (0.49 mmol) of 8-iodo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate and 115 mg (0.78 mmol) of 4-cyanophenylboronic acid to give, after purification by chromatography on silica (eluent dichloromethane/methanol 98/2) then recrystallization from methanol, 11 mg (6%) of 8-(4-cyano-phenyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a pale yellow solid.

Workup

  1. customThis compound is prepared
  2. customto give
  3. customafter purification by chromatography on silica (eluent dichloromethane/methanol 98/2)
  4. customrecrystallization from methanol, 11 mg (6%) of 8-(4-cyano-phenyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a pale yellow solid

Sources & evidence

ORD record
ord-44f4b54300804d2c8297988854afa19c
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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