Pyridine, 2-(trimethylstannyl)- → 3-Fluoro-5-(5-(2-pyridyl)-2-furyl)-benzonitrile

HRID 432009Notes

Reaction equation

Br[C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH:12]=[C:13]([F:15])[CH:14]=2)[C:10]#[N:11])=[CH:4][CH:3]=1.C[Sn](C)(C)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>C1(C)C=CC=CC=1.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>[F:15][C:13]1[CH:12]=[C:9]([CH:8]=[C:7]([C:5]2[O:6][C:2]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[CH:3][CH:4]=2)[CH:14]=1)[C:10]#[N:11]

Participants

Conditions

Temperature: 110 °C

Procedure

Pd(PPh3)4 (10 mg, 0.009 mmol) was added to a solution of 3-(5-bromofuran-2-yl)-5-fluoro-benzonitrile (180 mg, 86% purity, 0.59 mmol) and 2-trimethylstannylpyridine (193 mg, 0.80 mmol) in toluene (2.5 mL) under argon. The resulting solution was stirred at 110° C. for 48 h. After cooling to room temperature, the solvent was removed in vacuo. Flash chromatography (silica gel, 35-100% dichloromethane in hexane) afforded 67.7 mg (43%) of 3-fluoro-5-(5-(2-pyridyl)-2-furyl)-benzonitrile. 1H-NMR (CDCl3), δ (ppm): 8.64 (d, 1H), 7.76-7.83 (m, 3H), 7.66 (m, 1H), 7.24 (m, 2H), 7.19 (d, 1H), 6.92 (d, 1H).

Workup

temperatureAfter cooling to room temperature
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-e03b379264b242f38f277f4a21d643f5
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660753B2

Reaction notes

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