Citric Acid → {2-[(5-Vinyl-benzofuran-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester

HRID 1271873Notes

Reaction equation

[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23](Br)=[CH:22][C:20]=2[CH:21]=1)=[O:16])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].[CH2:31](OB(C=C)OCCCC)[CH2:32]CC.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C=CC=CC=1.CO>[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([CH:31]=[CH2:32])=[CH:22][C:20]=2[CH:21]=1)=[O:16])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 2027 mg (4.7 mmol) {2-[(5-Bromo-benzofuran-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester (56) and 289 mg (0.25 mmol) Pd(Ph3)4 in 40 ml toluene were added 1.84 ml of a 5.4M solution of sodium methoxide in methanol and 957 mg (5.2 mmol) vinylboronic acid dibutyl ester and the solution was heated at 90° C. for 3 h. The reaction mixture was poured on 5% aqueous citric acid. Extraction with ethyl acetate, washing of the organic phase with brine. The organic phase was dried over sodium sulfate, the solvent was evaporated and the residue subjected to silica gel chromatography (petrolether/ethylacetate 2:1) to give 1530 mg (4.04 mmol) {2-[(5-Vinyl-benzofuran-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester (57).

Workup

extractionExtraction with ethyl acetate
washwashing of the organic phase with brine
dry with materialThe organic phase was dried over sodium sulfate
customthe solvent was evaporated

Sources & evidence

ORD record: ord-2482a54683f845e787c19b6eb434933f
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208491B2

Reaction notes

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