2-Phenyl-2-propanol → (4,4-Difluoro-piperidin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1-(1-methyl-1-phenyl-ethyl)-1H-indol-2-yl]-methanone

HRID 1820468Notes

Reaction equation

HRID 1820468 reaction equation
[Cl-].C(C[P+](C)(C)C)#N.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:19]1([C:25](O)([CH3:27])[CH3:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[F:29][C:30]1([F:58])[CH2:35][CH2:34][N:33]([C:36]([C:38]2[NH:39][C:40]3[C:45]([CH:46]=2)=[CH:44][C:43]([C:47]([N:49]2[CH2:54][CH2:53][N:52]([CH:55]([CH3:57])[CH3:56])[CH2:51][CH2:50]2)=[O:48])=[CH:42][CH:41]=3)=[O:37])[CH2:32][CH2:31]1>>[F:58][C:30]1([F:29])[CH2:35][CH2:34][N:33]([C:36]([C:38]2[N:39]([C:25]([CH3:27])([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:26])[C:40]3[C:45]([CH:46]=2)=[CH:44][C:43]([C:47]([N:49]2[CH2:50][CH2:51][N:52]([CH:55]([CH3:56])[CH3:57])[CH2:53][CH2:54]2)=[O:48])=[CH:42][CH:41]=3)=[O:37])[CH2:32][CH2:31]1

Participants

5

Reactant 4

HCID 120532-Phenyl-2-propanolHCID 3251421Potassium bis(trimethylsilyl)amideHCID 57431663(Cyanomethyl)trimethylphosphonium chlorideHCID 68680853(4,4-Difluoro-piperidin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone

Product 1

HCID 68681432(4,4-Difluoro-piperidin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1-(1-methyl-1-phenyl-ethyl)-1H-indol-2-yl]-methanoneYield 9%

Procedure

The title compound was synthesized in analogy to example 74, from (cyanomethyl)trimethylphosphonium chloride (prepared according to Tetrahedron Lett. 1996, 37 (14), 2459-62), potassium bis(trimethylsilyl)amide, 2-phenyl-2-propanol and (4,4-difluoro-piperidin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone (example 32), to give the desired product as a yellow foam (9%).

Sources & evidence

ORD record
ord-7966e79b5e534798afae57e695840224
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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