Potassium Carbonate → 6-(5-(Cyclopropylcarbamoyl)-2-methylphenyl)-1-oxo-2-(pyridin-4-ylmethyl)-1,2-dihydroisoquinoline-4-carboxylic acid, methyl ester

HRID 907281Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)[CH:6]=[C:5]2[C:20]([O:22][CH3:23])=[O:21].[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>[CH:24]1([NH:27][C:28]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[C:31]([C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[C:8](=[O:12])[N:7]([CH2:13][C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)[CH:6]=[C:5]4[C:20]([O:22][CH3:23])=[O:21])[CH:30]=2)=[O:45])[CH2:25][CH2:26]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of the product of step i) (0.7 g), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.565 g) and potassium carbonate (0.518 g) in degassed N,N-dimethylformamide (15 mL) was treated with tetrakis(triphenylphosphine)palladium(0) (0.25 g) and the mixture heated at 80° C. under nitrogen for 40 hours. The reaction mixture was concentrated to dryness and the residue purified (SiO2, 5% methanol in dichloromethane as eluent) to give the sub-title compound (0.70 g).

Workup

concentrationThe reaction mixture was concentrated to dryness
customthe residue purified (SiO2, 5% methanol in dichloromethane as eluent)

Sources & evidence

ORD record: ord-fbe8a57d2b7e40d09abe50dc63e626cc
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012979B2

Reaction notes

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