Tributylvinyltin → 1-[(2-Methoxy-5-methylphenyl)sulfonyl]-4-vinyl-1H-indole

HRID 1159757Notes

Reaction equation

Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:11]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[O:21][CH3:22])(=[O:13])=[O:12].[CH2:23]([Sn](CCCC)(CCCC)C=C)[CH2:24]CC>C1(C)C=CC=CC=1.C([Sn](CCCC)(CCCC)C=C)CCC>[CH3:22][O:21][C:15]1[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:14]=1[S:11]([N:6]1[C:7]2[C:3](=[C:2]([CH:23]=[CH2:24])[CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1)(=[O:13])=[O:12]

Participants

Conditions

Temperature: 110 °C

Procedure

4-bromo-1-[(2-methoxy-5-methylphenyl)sulfonyl]-1H-indole (518 mg, 1.36 mmol; Intermediate 6), tributyl(vinyl)stannane (0.438 mL, 1.50 mmol) and Pd(PPh3)2OAc2 (51 mg, 0.068 mmol) were mixed in dry toluene (8 mL) and stirred 17 h at 110° C. using a STEM block. The mixture was filtered and additional tributyl(vinyl)stannane (0.200 mL, 0.68 mmol) and Pd(PPh3)2OAc2 (30 mg, 0.040 mmol) were added with continuous stirring for 23 h. Same procedure was repeated once more (additional reagents) with continuous stirring 24 h gave full conversion. The mixture was filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (DCM/hexane 2:3). This gave the desired product (2.62 g, 59%) as an off white solid. MS (ESI+) for C18H17NO3S m/z 328 (M+H)+.

Workup

filtrationThe mixture was filtered
stirringwith continuous stirring for 23 h
stirringwith continuous stirring 24 h
customgave full conversion
filtrationThe mixture was filtered
concentrationconcentrated under reduced pressure
customThe crude product was purified by flash chromatography (DCM/hexane 2:3)

Sources & evidence

ORD record: ord-0a7bb8b303df4990ab41d4389030973f
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812017B2

Reaction notes

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