Tributylvinyltin → 2-(2-chloro-5-vinylpyridin-4-yl)-4-fluoro-1H-indole

HRID 595674Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:8]=[N:9][C:10]([Cl:23])=[CH:11][C:12]=1[C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[C:19]([F:22])[CH:18]=[CH:17][CH:16]=2)(=O)=O.[Li+].[Cl-].[CH2:28]([Sn](CCCC)(CCCC)C=C)[CH2:29]CC>CN(C=O)C.O>[Cl:23][C:10]1[CH:11]=[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)[C:7]([CH:28]=[CH2:29])=[CH:8][N:9]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl trifluoromethanesulfonate (50 mg, 0.12 mmol), LiCl (8 mg, 0.19 mmol) in DMF (0.8 mL) was added tributyl(vinyl)stannane (80 mg, 0.25 mmol) dropwise at 25° C. under nitrogen. The mixture was stirred at 65° C. for 10 hours. The mixture was diluted with H2O, extracted with EtOAc, then the combined organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo to give the crude product. It was purified by column (PE:EA=5:1) to obtain the product of 2-(2-chloro-5-vinylpyridin-4-yl)-4-fluoro-1H-indole (150 mg, yield: 40%). 1H-NMR (CDCl3, 400 MHz) δ 8.45 (s, 1H), 7.41 (s, 1H), 7.15 (d, J=2.4 Hz, 1H), 6.88 (d, J=6.0 Hz, 1H), 6.79 (t, J=6.0 Hz, 1H), 6.35˜6.41 (m, 1H), 6.07˜6.10 (m, 1H), 5.77 (d, J=17.6 Hz, 1H), 5.49˜5.62 (m, 2H). MS (M+H)+: 273/275.

Workup

extractionextracted with EtOAc
washthe combined organic phase was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customto give the crude product
customIt was purified by column (PE:EA=5:1)

Sources & evidence

ORD record: ord-0b3c826eb1d3468f9c000ec7edc9eaec
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09243002B2

Reaction notes

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