(4-Bromophenylethynyl)trimethylsilane → Tert-butyl 4-(4-((trimethylsilyl)ethynyl)phenyl)piperidine-1-carboxylate

HRID 1487940Notes

Reaction equation

HRID 1487940 reaction equation
N1C2C(=CC([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)=CC=2)C=N1.Br[C:24]1[CH:29]=[CH:28][C:27]([C:30]#[C:31][Si:32]([CH3:35])([CH3:34])[CH3:33])=[CH:26][CH:25]=1>>[CH3:33][Si:32]([C:31]#[C:30][C:27]1[CH:28]=[CH:29][C:24]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:25][CH:26]=1)([CH3:34])[CH3:35]

Participants

3

Reactant 2

HCID 4226980(4-Bromophenylethynyl)trimethylsilane2×HCID 49760224tert-butyl 4-(1H-indazol-5-yl)piperidine-1-carboxylate

Product 1

HCID 59805220Tert-butyl 4-(4-((trimethylsilyl)ethynyl)phenyl)piperidine-1-carboxylateYield 67%

Procedure

The title compound was prepared using standard chemical manipulations and procedures similar to those used for the preparation of compound 62.4, except ((4-bromophenyl)ethynyl)trimethylsilane (compound 76.1, 850 mg, 3.36 mmol) was used in place of 5-bromo-1H-indazole to yield the title compound as a yellow oil (0.80 g, 67%).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-fb90edc3c8714951af9a4810433690d1
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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