Potassium Carbonate → 2-Benzyl-6-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid, methyl ester

HRID 907277Notes

Reaction equation

HRID 907277 reaction equation
[CH2:1]([N:8]1[CH:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24]1([NH:27][C:28](=[O:45])[C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[C:31](B3OC(C)(C)C(C)(C)O3)[CH:30]=2)[CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[CH:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:31]3[CH:30]=[C:29]([C:28](=[O:45])[NH:27][CH:24]4[CH2:26][CH2:25]4)[CH:34]=[CH:33][C:32]=3[CH3:35])[CH:14]=2)[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 575517152-Benzyl-6-bromo-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid, methyl ester

Product 1

HCID 575517342-Benzyl-6-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid, methyl ester

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the product of step i) (0.37 g), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.29 g) [prepared as described in US2005020590] and potassium carbonate (0.27 g) in degassed N,N-dimethylformamide (8 mL) was treated with tetrakis(triphenylphosphine)palladium(0) (0.115 g) and the mixture heated at 80° C. under nitrogen for 24 hours. The reaction mixture was concentrated to dryness and the crude product purified (SiO2, 2% methanol in dichloromethane as eluent) to give the sub-title compound (0.44 g).

Workup

  1. customprepared
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customthe crude product purified (SiO2, 2% methanol in dichloromethane as eluent)

Sources & evidence

ORD record
ord-b75a41df79fb4300adf84c185f5dce3b
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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