tert-Butyl 2-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[indoline-3,4'-piperidine]-1'-carboxylate → 3,3-Difluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-2-one

HRID 2209287Notes

Reaction equation

HRID 2209287 reaction equation
O=C1C2(CCN(C(OC(C)(C)C)=O)CC2)C2C(=CC([B:23]3[O:27][C:26]([CH3:29])([CH3:28])[C:25]([CH3:31])([CH3:30])[O:24]3)=CC=2)N1.Br[C:33]1[CH:41]=[C:40]2[C:36]([C:37]([F:52])([F:51])[C:38](=[O:50])[N:39]2[CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])=[CH:35][CH:34]=1>>[F:51][C:37]1([F:52])[C:36]2[C:40](=[CH:41][C:33]([B:23]3[O:27][C:26]([CH3:29])([CH3:28])[C:25]([CH3:31])([CH3:30])[O:24]3)=[CH:34][CH:35]=2)[N:39]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[C:38]1=[O:50]

Participants

3

Reactant 2

HCID 92133768tert-Butyl 2-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[indoline-3,4'-piperidine]-1'-carboxylateHCID 1234084286-Bromo-3,3-difluoro-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-2-one

Product 1

HCID 1238728503,3-Difluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-2-one

Procedure

Following the procedure described for intermediate 7.33 (Step 2), starting from 6-bromo-3,3-difluoro-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-2-one 7.35 (84 mg), 94 mg of crude 3,3-difluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-2-one 7.36 was obtained. This material was used without further purification.

Sources & evidence

ORD record
ord-041280efc1b74ddd86a02884e5d13b0b
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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