Tributylvinyltin → N-(2-Methoxy-5-methylphenyl)-7-vinyl-1-benzofuran-5-sulfonamide

HRID 1162041Notes

Reaction equation

I[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([S:11]([NH:14][C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])(=[O:13])=[O:12])[CH:3]=1.[CH2:24]([Sn](CCCC)(CCCC)C=C)[CH2:25]CC>C(#N)C>[CH3:23][O:22][C:16]1[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:15]=1[NH:14][S:11]([C:4]1[CH:3]=[C:2]([CH:24]=[CH2:25])[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=1)(=[O:13])=[O:12]

Participants

Conditions

Temperature: 180 °C

Procedure

Five batches each consisting of a mixture of N-(2-methoxy-5-methylphenyl)-7-iodo-1-benzofuran-5-sulfonamide (443 mg, 1.0 mmol; Intermediate 57), tributyl(vinyl)tin (350 mg, 1.1 mmol) and bis(triphenylphosphine)palladium diacetate (15 mg, 0.02 mmol) in acetonitrile (3 mL) was heated in a Smith Creator microwave oven to 180° C. for 5 min. The combined reaction mixtures were filtered and concentrated to give 2.0 g of crystalline crude material that was put through a SiO2 column using EtOAc/hexane (gradient 5:95→25:75) as eluent giving 1.3 g (75%) of off-white crystalline product. 1H NMR (400 MHz, CDCl3) δ 2.26 (s, 3H), 3.53 (s, 3H), 5.56 (dd, 1H), 6.16 (dd, 1H), 6.57 (d, 1H), 6.79-6.98 (m, 4H), 7.38 (d, 1H), 7.71-7.74 (m, 2H), 7.94 (d, 1H); MS (ESI+) for C18H17NO4S m/z 344 (M+H)+.

Workup

customThe combined reaction mixtures
filtrationwere filtered
concentrationconcentrated

Sources & evidence

ORD record: ord-a48bb0a2064d41cba4e81cd3335f74c2
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820675B2

Reaction notes

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