Tributylvinyltin → 1-{[3-(Trifluoromethyl)phenyl]sulfonyl}-4-vinyl-1H-indole

HRID 1159767Notes

Reaction equation

HRID 1159767 reaction equation
C[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[C:19]2[C:14](=[C:15]([CH:20]=[CH2:21])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)(=[O:10])=[O:9].BrC1C=CC=C2C=1C=CN2S(C1C=CC=C([C:41]([F:44])([F:43])[F:42])C=1)(=O)=O.C([Sn](CCCC)(CCCC)C=C)CCC>>[F:42][C:41]([F:44])([F:43])[C:5]1[CH:4]=[C:3]([S:8]([N:11]2[C:19]3[C:14](=[C:15]([CH:20]=[CH2:21])[CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)(=[O:10])=[O:9])[CH:2]=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 81998TributylvinyltinHCID 68713053HCID 68713053, compoundHCID 68717330HCID 68717330, compound2×

Product 1

HCID 687142331-{[3-(Trifluoromethyl)phenyl]sulfonyl}-4-vinyl-1H-indoleYield 80%

Procedure

The experimental for Intermediate 15 was followed using 4-bromo-1-{[3-(trifluoromethyl)phenyl]sulfonyl}-1H-indole (500 mg, 1.24 mmol; Intermediate 17), tributyl(vinyl)stannane (tot 0.723 mL, 2.86 mmol) and Pd(PPh3)2OAc2 (tot 46 mg, 0.062 mmol). The title compound (348 mg, 80%) was obtained as a yellow sticky oil. MS (ESI+) for C17H12F3NO2S m/z 352 (M+H)+.

Sources & evidence

ORD record
ord-995c8f879523403090b54d95d801e65b
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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