4-Piperidinecarboxamide → 1-{4-[2-Benzyl-7-(trifluoromethyl)-2H-indazol-3-YL]phenyl}piperidine-4-carboxamide

HRID 735442Notes

Reaction equation

HRID 735442 reaction equation
[CH2:1]([N:8]1[C:16]([C:17]2[CH:22]=[CH:21][C:20](Cl)=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([C:24]([F:27])([F:26])[F:25])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:28]1[CH2:36][CH2:35][CH:31]([C:32]([NH2:34])=[O:33])[CH2:30][CH2:29]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC(C)([O-])C.[Na+]>C(COC)OC>[CH2:1]([N:8]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([N:28]3[CH2:36][CH2:35][CH:31]([C:32]([NH2:34])=[O:33])[CH2:30][CH2:29]3)=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([C:24]([F:27])([F:26])[F:25])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 37724-PiperidinecarboxamideHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 670211872-benzyl-3-(4-chlorophenyl)-7-(trifluoromethyl)-2H-indazole

Product 1

HCID 115837851-{4-[2-Benzyl-7-(trifluoromethyl)-2H-indazol-3-YL]phenyl}piperidine-4-carboxamideYield 28.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2-benzyl-3-(4-chlorophenyl)-7-(trifluoromethyl)-2H-indazole (0.1 g, 0.25 mmol), isonipecotamide (0.039 g, 0.3 mmol), tris-(dibenzylidineacetone)dipalladium(0) (14 mg), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (47 mg) and sodium t-butoxide (0.029 g, 0.3 mmol) in 2 mL of dimethoxyethane was heated at 150° C. for 5 minutes in a microwave (Emory's Optimizer, Personal Chemistry). The reaction mixture was concentrated in vacuo. The residue was purified by flash chromatography (CH2Cl2-CH3OH, 19:1) to give the product (0.034 g) as an off-white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by flash chromatography (CH2Cl2-CH3OH, 19:1)

Sources & evidence

ORD record
ord-663709a305934b70b960e1cc39f0ad53
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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