Triethylsilane → HCID 59332647, compound
Reaction equation
[C:1]1([CH:7]2[CH2:12][C:11](=O)[CH2:10][CH2:9][S:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[Br:26][C:27]1[CH:28]=[C:29]2[C:33](=[C:34]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:35]=1)[NH:32][CH:31]=[CH:30]2.C([SiH](CC)CC)C>ClCCl>[Br:26][C:27]1[CH:28]=[C:29]2[C:33](=[C:34]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:35]=1)[NH:32][CH:31]=[C:30]2[CH:11]1[CH2:10][CH2:9][S:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12]1Participants
Procedure
To a solution of 2-phenylthian-4-one (SJTU) (0.900 g, 4.68 mmol) in dichloromethane (DCM) (15 mL), cooled on an ice bath to 0° C., under argon, was added dropwise trimethylsilyl trifluoromethanesulfonate (1.807 mL, 10 mmol) over 10 minutes, an additional portion of dry DCM (5 mL) was used to wash the addition funnel walls. To this mixture ethyl 5-bromo-1H-indole-7-carboxylate (1.340 g, 5.00 mmol) was added dropwise, in solution with of dry DCM, over 2 hours. Finally, triethylsilane (3.19 mL, 20 mmol) was added in one portion and the mixture was stirred 2 h at ca 0° C., and left stirring at 23° C. 16 h. The reaction was quenched with a saturated aqueous solution of sodium bicarbonate, and the resulting biphasic mixture partitioned with DCM to afford 2.21 g of brow gummy oil. LCMS of product may indicate an overlapping mixture of ca 5:2 major to minor isomers (cis/trans).
Workup
- washto wash the addition funnel walls
- waitleft
- stirringstirring at 23° C
- custom16 h
- customThe reaction was quenched with a saturated aqueous solution of sodium bicarbonate
- customthe resulting biphasic mixture partitioned with DCM
- customto afford 2.21 g of brow gummy oil
- additionan overlapping mixture of ca 5:2 major to minor isomers (cis/trans)
Sources & evidence
- ORD record
- ord-5604efa4783b482da2578e2d49b5a414
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372875B2
Reaction notes
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