Tributylvinyltin → HCID 90333585, compound

HRID 595685Notes

Reaction equation

HRID 595685 reaction equation
FC(F)(F)S(O[C:7]1[C:12]([C:13]2[NH:14][C:15]3[C:20]([CH:21]=2)=[C:19]([F:22])[CH:18]=[CH:17][CH:16]=3)=[N:11][C:10]([C:23]2[C:24]([N:43]([CH3:48])[S:44]([CH3:47])(=[O:46])=[O:45])=[CH:25][C:26]3[O:30][C:29]([C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)=[C:28]([C:38](=[O:41])[NH:39][CH3:40])[C:27]=3[CH:42]=2)=[CH:9][N:8]=1)(=O)=O.[CH2:51]([Sn](CCCC)(CCCC)C=C)[CH2:52]CC.[Li+].[Cl-]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:22][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:20]=1[CH:21]=[C:13]([C:12]1[N:11]=[C:10]([C:23]3[C:24]([N:43]([CH3:48])[S:44]([CH3:47])(=[O:45])=[O:46])=[CH:25][C:26]4[O:30][C:29]([C:31]5[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=5)=[C:28]([C:38]([NH:39][CH3:40])=[O:41])[C:27]=4[CH:42]=3)[CH:9]=[N:8][C:7]=1[CH:51]=[CH2:52])[NH:14]2

Participants

6

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 90333728HCID 90333728, compound

Product 1

HCID 90333585HCID 90333585, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 3-(4-fluoro-1H-indol-2-yl)-5-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)pyrazin-2-yl trifluoromethanesulfonate (30 mg, 0.04 mmol), tributyl(vinyl)stannane (16 mg, 0.05 mmol) and LiCl (5 mg, 0.12 mmol) in DMF (1 mL) was added Pd(PPh3)2Cl2 (5 mg) under nitrogen atmosphere. The reaction mixture was stirred at 60° C. for 1 h, concentrated and purified by prep-TLC (PE:EA=1:1) to give 5-(6-(4-fluoro-1H-indol-2-yl)-5-vinylpyrazin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (15 mg, yield: 60%). 1H-NMR (CDCl3, 400 MHz) δ 8.66 (s, 1H), 8.10 (s, 1H), 7.86˜7.89 (m, 2H), 7.57˜7.61 (m, 2H), 7.38˜7.44 (m, 3H), 7.04˜7.19 (m, 3H), 6.71 (t, J=8.0 Hz, 1H), 6.50˜6.54 (m, 1H), 5.89 (br s, 1H), 5.71˜5.74 (m, 1H), 3.11 (s, 3H), 2.91 (s, 6H). MS (M+H)+: 614.

Workup

  1. concentrationconcentrated
  2. custompurified by prep-TLC (PE:EA=1:1)

Sources & evidence

ORD record
ord-7ff50225ec0a4df58c71ac461cdd3587
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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