Sodium Carbonate → Methyl 7-(4-hydroxyphenyl)-3-isoquinolinecarboxylate

HRID 2423404Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[N:13]=[CH:14]2)=[CH:9][CH:8]=1)(=O)=O.CC1(C)C(C)(C)OB([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[OH:37][C:34]1[CH:35]=[CH:36][C:31]([C:7]2[CH:16]=[C:15]3[C:10]([CH:11]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[N:13]=[CH:14]3)=[CH:9][CH:8]=2)=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of 700 mg (2.09 mmol) of methyl 7-{[(trifluoromethyl)sulfonyl]oxy}-3-isoquinolinecarboxylate, 715 mg (3.13 mmol) of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 240 mg (0.21 mmol) of tetrakistriphenylphosphine palladium(0) and 3.70 mL (3.31 mmol) of 2.0 M Na2CO3 (aq) in 10 mL of 1,2-dimethoxyethane was stirred at 90° C. for 20 min. The suspension was filtered through a pad of Celite® and the filter cake was washed with EtOAc. The combined organics were then evaporated and the residue purified by silica gel chromatography (40 g of silica gel eluting with 0-15% acetone in CH2Cl2 over 45 minutes) to give 360 mg (62%) of methyl 7-(4-hydroxyphenyl)-3-isoquinolinecarboxylate as a beige solid. 1H NMR (400 MHz, DMSO-d6): δ 9.75 (s, 1H), 9.38 (s, 1H), 8.42 (s, 1H), 8.23 (s, 1H), 8.21 (d, J=8 Hz, 1H), 8.15 (d, J=8 Hz, 1H), 7.72 (d, J=9 Hz, 2H), 6.91 (d, J=9 Hz, 2H), 3.91 (s, 3H). ESI-LCMS m/z 280 (M+H)+.

Workup

filtrationThe suspension was filtered through a pad of Celite®
washthe filter cake was washed with EtOAc
customThe combined organics were then evaporated
customthe residue purified by silica gel chromatography (40 g of silica gel eluting with 0-15% acetone in CH2Cl2 over 45 minutes)

Sources & evidence

ORD record: ord-a368396908a9408784c4d37fa8d0ed8e
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960552B2

Reaction notes

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