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

HRID 217341Notes

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-ff950319ee1749528efe798e02b853b5
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193368B2

Reaction notes

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