Hexamethylditin → HCID 21942444, compound

HRID 432004Notes

Reaction equation

C[Sn](C)C.C[Sn](C)C.Br[C:10]1[O:14][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:12][CH:11]=1.Br[C:22]1[CH:23]=[C:24]([N:29]2[CH:33]=[CH:32][N:31]=[CH:30]2)[CH:25]=[C:26]([F:28])[CH:27]=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>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:13]1[O:14][C:10]([C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([N:29]3[CH:33]=[CH:32][N:31]=[CH:30]3)[CH:23]=2)=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Title compound synthesis: Pd(PPh3)4 (10 mg, 0.009 mmol) was added to a solution of hexamethylditin (169 mg, 0.52 mmol) and 5-bromo-2-(2-pyridyl)-furan (90 mg, 88% purity, 0.36 mmol) in toulene (2 mL) under argon. The resulting solution was stirred at 80° C. for 19 h. After cooling to room temperature, a second portion of Pd(PPh3)4 (10 mg, 0.009 mmol) and 1-(3-bromo-5-fluoro-phenyl)-lH-imidazole (86 mg, 0.36 mmol) were added and the resulting solution was stirred at 110° C. for 36 h. After cooling to room temperature, the solvent was removed in vacuo. Chromatography (5g silica gel SPE tube, 0-3% methanol in 1:1 chloroform:ethyl acetate) afforded 72.3 mg (66%) of 2-(2-pyridyl)-5-(5-fluoro-3-(1-imidazolyl)phenyl)-furan. 1H-NMR (CDCl3), δ (ppm): 8.63 (d, 1H), 7.93 (s, 1H), 7.78 (m, 2H), 7.57 (s, 1H), 7.45 (m, 1H), 7.35 (s, 1H), 7.23 (m, 3H), 7.03 (m, 1H), 6.91 (d, 1H).

Workup

temperatureAfter cooling to room temperature
stirringthe resulting solution was stirred at 110° C. for 36 h
temperatureAfter cooling to room temperature
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-740891f5a2c34d3287aaaef25c0b1dcd
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660753B2

Reaction notes

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