Benzyl Alcohol → HCID 68684335, compound

HRID 1820388Notes

Reaction equation

HRID 1820388 reaction equation
[F:1][C:2]1([F:30])[CH2:7][CH2:6][N:5]([C:8]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([C:19]([N:21]2[CH2:26][CH2:25][N:24]([CH:27]([CH3:29])[CH3:28])[CH2:23][CH2:22]2)=[O:20])=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]1.[CH2:31](O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C1(P(=CC#N)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:31]([N:11]1[C:12]2[C:17](=[CH:16][C:15]([C:19]([N:21]3[CH2:22][CH2:23][N:24]([CH:27]([CH3:28])[CH3:29])[CH2:25][CH2:26]3)=[O:20])=[CH:14][CH:13]=2)[CH:18]=[C:10]1[C:8]([N:5]1[CH2:6][CH2:7][C:2]([F:1])([F:30])[CH2:3][CH2:4]1)=[O:9])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 85524(Triphenylphosphoranylidene)acetonitrileHCID 68680853(4,4-Difluoro-piperidin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone

Product 1

HCID 68684335HCID 68684335, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The suspension of 0.15 g (0.36 mmol) (4,4-difluoro-piperidin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone (example 32), 72 μL (76 mg, 0.72 mmol) benzylalcohol and 173 mg (0.72 mmol) (triphenylphosphoranylidene)acetonitrile in 2 mL toluene was stirred for 3 hours under reflux. The volatile components were evaporated at a rotary evaporator and the residue was purified using flash chromatography on silica gel with dichloromethane:methanol (19:1 v/v) as eluant to give 0.11 g (63%) of the desired compound as a light brown foam.

Workup

  1. temperatureunder reflux
  2. customThe volatile components were evaporated at a rotary evaporator
  3. customthe residue was purified

Sources & evidence

ORD record
ord-2b9a3393d0b64654802a50693fe879aa
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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