Tributylvinyltin → HCID 24957619, compound

HRID 244429Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]([C:26]3[CH:27]=[C:28]4[C:32](=[CH:33][CH:34]=3)[N:31]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)[N:30]=[CH:29]4)([OH:25])[C:21]([F:24])([F:23])[F:22])=[CH:7][N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[CH2:42]([Sn](CCCC)(CCCC)C=C)[CH2:43]CC>C1(C)C=CC=CC=1>[F:24][C:21]([F:22])([F:23])[C:20]([C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[N:31]([C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=1)[N:30]=[CH:29]2)([C:6]1[C:5]2[C:9](=[CH:10][C:2]([CH:42]=[CH2:43])=[CH:3][CH:4]=2)[N:8]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[CH:7]=1)[OH:25]

Participants

Conditions

Temperature: 100 °C

Procedure

To a room temperature solution of 0.25 g (0.4 mmol) of 1-[6-bromo-1-(4-methoxybenzyl)-1H-indol-3-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol in toluene was added 0.13 g (0.4 mmol) of tri-n-butyl(vinyl)tin. After 15 minutes, 3.0 mg of dichlorobis(triphenylphosphine)Pd (II) was added and the reaction was warmed to 100° C. and stirred overnight. The mixture was then cooled to room temperature, filtered through a pad of CELITE® filter aid, and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate-hexanes (5-20% gradient) to afford 0.1 g (44%) of the title compound. MS m/z 572.6 (MH+).

Workup

temperatureThe mixture was then cooled to room temperature
filtrationfiltered through a pad of CELITE®
filtrationfilter aid
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-fea88ece008044139d9954ce23fe508c
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658637B2

Reaction notes

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