Methanol → HCID 68717796, compound

HRID 1159774Notes

Reaction equation

HRID 1159774 reaction equation
C[C:2]1C=[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=C[N:27]2S(C1C=NC=CC=1)(=O)=O.C([Sn](CCCC)(CCCC)C=C)CCC.CO>CC#N.C(Cl)Cl>[N:27]1[CH:6]=[CH:5][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]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 81998TributylvinyltinHCID 68712618HCID 68712618, compound2×HCID 68713053HCID 68713053, compound

Product 1

HCID 68717796HCID 68717796, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

The experimental for Intermediate 15 was followed using 4-bromo-1-(pyridin-3-ylsulfonyl)-1H-indole (285 mg, 0.85 mmol; Intermediate 24) in dry MeCN (5 mL, one vial), tributyl(vinyl)stannane (0.494 mL, 1.69 mmol) and Pd(PPh3)2OAc2 (32 mg, 0.042 mmol). Flash chromatography (1% MeOH in DCM) afforded the title compound (208 mg, 80%) as a yellow sticky oil. MS (ESI+) for C15H12N2O2S m/z 285 (M+H)+.

Sources & evidence

ORD record
ord-f2b4251a612b4e71b2bacf68998be07d
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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