Cesium carbonate → 2'-Fluoro-4'-methyl-5-tetrazol-1-yl-biphenyl-3-carboxylic acid (1-furan-2-yl-ethyl)-amide

HRID 77766Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([NH:8][C:9](=[O:22])[C:10]1[CH:15]=[C:14]([N:16]2[CH:20]=[N:19][N:18]=[N:17]2)[CH:13]=[C:12](I)[CH:11]=1)[CH3:7].[F:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1COCC1.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>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([NH:8][C:9]([C:10]1[CH:11]=[C:12]([C:25]2[CH:26]=[CH:27][C:28]([CH3:30])=[CH:29][C:24]=2[F:23])[CH:13]=[C:14]([N:16]2[CH:20]=[N:19][N:18]=[N:17]2)[CH:15]=1)=[O:22])[CH3:7]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of N-(1-Furan-2-yl-ethyl)-3-iodo-5-tetrazol-1-yl-benzamide (60 mg, 0.146 mmol), 2-fluoro-4-methyl-phenylboronic acid (27.1 mg, 0.176 mmol), Cs2CO3 (0.35 mL, 0.5 N, 0.176 mmol) and Pd(Ph3P)4 (8.5 mg, 0.00735 mmol) in toluene (1.5 mL) and THF (1.5 mL) was stirred under microwave heating for 30 minutes at 130° C. After reaction mixture was cooled down, the solvent was removed under vacuum and the residue was purified by column chromatography (hexane/EtOAc=1:2) to afford 2′-Fluoro-4′-methyl-5-tetrazol-1-yl-biphenyl-3-carboxylic acid (1-furan-2-yl-ethyl)-amide as a white solid (57 mg, 98%). MS (M+H)=392.

Workup

customAfter reaction mixture
temperaturewas cooled down
customthe solvent was removed under vacuum
customthe residue was purified by column chromatography (hexane/EtOAc=1:2)

Sources & evidence

ORD record: ord-97f7494a2c314428a791ef06dcb9ed07
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841336B2

Reaction notes

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