Water → HCID 86682976, compound

HRID 1497132Notes

Reaction equation

HRID 1497132 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:23])[NH:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11](Br)=[CH:10][C:9]=2[CH3:22])=[O:4].[CH2:24](B(CC)CC)[CH3:25].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:23])[NH:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([CH2:24][CH3:25])=[CH:10][C:9]=2[CH3:22])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 7357TriethylboraneHCID 11430Potassium CarbonateHCID 86682977HCID 86682977, compound

Product 1

HCID 86682976HCID 86682976, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 6-bromo-8-methyl-2-oxo-4-phenyl-1,2-dihydro-quinoline-3-carboxylic acid methyl ester (25 mg, 67.2 μmol, Eq: 1.00), triethylborane (134 μl, 134 μmol, Eq: 2), potassium carbonate (18.6 mg, 134 μmol, Eq: 2) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (5.49 mg, 6.72 μmol, Eq: 0.1) in DMF was heated to 65° C. for 16 h in a sealed tube. Then water was added and the reaction mixture was extracted with ethyl acetate (3×). The combined extracts were washed with water and brine, dried with Na2SO4 and evaporated. The remaining residue was purified by column chromatography (silica gel, DCM/EtOAc 4:1) to afford the title compound as light brown solid (15 mg). MS (ESI): 322.2 (M+H)+.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (3×)
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customThe remaining residue was purified by column chromatography (silica gel, DCM/EtOAc 4:1)

Sources & evidence

ORD record
ord-716722ef63864834b46ec089734a1c0e
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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