4-Fluorophenylboronic acid → HCID 67036322, compound

HRID 1623478Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2I)[C:12](=[O:16])[C:13]#[C:14][CH3:15])[CH:5]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.S1C=CC=C1C(O)=O.[Cu]>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13](=[C:14]([C:29]3[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=3)[CH3:15])[C:12]2=[O:16])[CH:5]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 3-{[(2-iodo-phenyl)-(1-oxo-but-2-ynyl)-amino]-methyl}-benzoic acid methyl ester (0.5 g, 1.15 mmol), 4-fluorophenylboronic acid (0.32 g, 2.3 mmol), tetrakis(triphenylphosphine) palladium (0.13 g, 0.115 mmol) and copper thiophene-2-carboxylic acid (0.46 g, 2.42 mmol) in THF was stirred for 5 hours at 60° C. After removal of solvent, the residue was purified by flash chromatography, eluting with ethyl acetate/hexane=1:5 to afford the product 3-{3-[1-(4-fluoro-phenyl)-ethylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester (0.28 g, 60%) as a yellow solid. MS calcd. for C25H20FNO3 401.4, obsd. (ESI+) [(M+H)+] 402.2.

Workup

customAfter removal of solvent
customthe residue was purified by flash chromatography
washeluting with ethyl acetate/hexane=1:5

Sources & evidence

ORD record: ord-214845974239423fbfb9756e79dab465
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778973B2

Reaction notes

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