Tetrabutylammonium Fluoride → Methyl 3-cyclohexyl-2-[2-(hydroxymethyl)-4-methoxyphenyl]-1-prop-2-yn-1-yl-1H-indole-6-carboxylate

HRID 1518262Notes

Reaction equation

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH:19]1([C:25]2[C:33]3[C:28](=[CH:29][C:30]([C:34]([O:36][CH3:37])=[O:35])=[CH:31][CH:32]=3)[N:27]([CH2:38][C:39]#[CH:40])[C:26]=2[C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][C:42]=2[CH2:49][O:50][Si](C(C)C)(C(C)C)C(C)C)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C1COCC1.CCOC(C)=O>[CH:19]1([C:25]2[C:33]3[C:28](=[CH:29][C:30]([C:34]([O:36][CH3:37])=[O:35])=[CH:31][CH:32]=3)[N:27]([CH2:38][C:39]#[CH:40])[C:26]=2[C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][C:42]=2[CH2:49][OH:50])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 0 °C

Procedure

Tetrabutylammonium fluoride (1.3 eq., 1M solution in THF) was added dropwise to an ice cooled solution of methyl 3-cyclohexyl-2-(4-methoxy-2-{[(triisopropylsilyl)oxy]methyl}phenyl)-1-prop-2-yn-1-yl-1H-indole-6-carboxylate in THF (0.036M). The mixture was stirred at 0° C. for 1 h then diluted with EtOAc, washed with saturated aq. NH4Cl, water and brine. The organic phase was dried over Na2SO4 and evaporated in vacuo. The residual material was subjected to flash chromatography (PE:EtOAc, 3:1). After evaporation of the solvent the product was obtained as white solid (64%). MS (ES+): 432.5 (M+H+).

Workup

washwashed with saturated aq. NH4Cl, water and brine
dry with materialThe organic phase was dried over Na2SO4
customevaporated in vacuo
customAfter evaporation of the solvent the product

Sources & evidence

ORD record: ord-113387404cd845a4a2130d12b5810501
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232390B2

Reaction notes

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