4-Fluorobenzylic alcohol → HCID 68681673, compound

HRID 2241574Notes

Reaction equation

HRID 2241574 reaction equation
[Cl-].C(C[P+](C)(C)C)#N.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]O)=[CH:22][CH:21]=1.[F:28][C:29]1([F:57])[CH2:34][CH2:33][N:32]([C:35]([C:37]2[NH:38][C:39]3[C:44]([CH:45]=2)=[CH:43][C:42]([C:46]([N:48]2[CH2:53][CH2:52][N:51]([CH:54]([CH3:56])[CH3:55])[CH2:50][CH2:49]2)=[O:47])=[CH:41][CH:40]=3)=[O:36])[CH2:31][CH2:30]1>C1(C)C=CC=CC=1>[F:57][C:29]1([F:28])[CH2:34][CH2:33][N:32]([C:35]([C:37]2[N:38]([CH2:24][C:23]3[CH:26]=[CH:27][C:20]([F:19])=[CH:21][CH:22]=3)[C:39]3[C:44]([CH:45]=2)=[CH:43][C:42]([C:46]([N:48]2[CH2:49][CH2:50][N:51]([CH:54]([CH3:55])[CH3:56])[CH2:52][CH2:53]2)=[O:47])=[CH:41][CH:40]=3)=[O:36])[CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 680224-Fluorobenzylic alcoholHCID 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 68681673HCID 68681673, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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, 4-fluorobenzylalcohol and (4,4-difluoro-piperidin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone (example 32) in toluene to give the compound as a colorless foam (37%).

Sources & evidence

ORD record
ord-1312826dd10243cd8362f75bbc5f3a60
Source dataset
uspto-grants-2010_05
Patent number
US07723325B2

Reaction notes

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