Water → 3-Methyl-4-pyridin-3-yl-benzofuran-2-carboxylic acid tert-butyl ester

HRID 29364Notes

Reaction equation

[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14](OS(C(F)(F)F)(=O)=O)[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[N:32]1[CH:37]=[CH:36][CH:35]=[C:34](B(O)O)[CH:33]=1.O>COCCOC>[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([C:34]3[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=3)[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

To 3-methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid tert-butyl ester (285 mg, 0.75 mmol) in 3 mL of 1,2-dimethoxyethane was added K2CO3 (363 mg, 3.5 eq), pyridine-3-boronic acid (138 mg, 1.13 mmol), Pd(Ph3)4 (43 mg, 0.05 eq), and 0.5 mL of water. The mixture was heated and stirred in an 85° C. oil bath for 3 h. The reaction mixture was poured into water and was extracted with ethyl acetate. The organic extract was washed with water and dried over sodium sulfate. Removal of the solvent in vacuo gave the crude product, which was purified by column chromatography to give 202 mg of 3-methyl-4-pyridin-3-yl-benzofuran-2-carboxylic acid tert-butyl ester, obtained as white solid.

Workup

temperatureThe mixture was heated
extractionwas extracted with ethyl acetate
extractionThe organic extract
washwas washed with water
dry with materialdried over sodium sulfate
customRemoval of the solvent in vacuo
customgave the crude product, which
customwas purified by column chromatography

Sources & evidence

ORD record: ord-941d6f5d11d54128bc0c2910058d1d60
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420001B2

Reaction notes

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