(Trifluoromethyl)trimethylsilane → HCID 68379820, compound

HRID 2178722Notes

Reaction equation

HRID 2178722 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12](B(O)O)[N:13]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)[C:30]([F:33])([F:32])[F:31]>>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:30]([F:33])([F:32])[F:31])[N:13]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2763172[4-(Benzyloxy)-1-(tert-butoxycarbonyl)-1H-indol-2-yl]boronic acid

Product 1

HCID 68379820HCID 68379820, compound

Procedure

[4-(Benzyloxy)-1-(tert-butoxycarbonyl)-1H-indol-2-yl]boronic acid and trimethyl(trifluoromethyl)silane were combined to give tert-butyl 4-(benzyloxy)-2-(trifluoromethyl)-1H-indole-1-carboxylate, which was debenzylated via ammonium formate transfer hydrogenation to give tert-butyl 4-hydroxy-2-(trifluoromethyl)-1H-indole-1-carboxylate.

Sources & evidence

ORD record
ord-0b31fb715f954818830d8cf5b1d74677
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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