Pyridine → HCID 68682179, compound

HRID 2241549Notes

Reaction equation

HRID 2241549 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.[CH3:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:30][C:2]1([F:1])[CH2:7][CH2:6][N:5]([C:8]([C:10]2[N:11]([C:35]3[CH:36]=[CH:37][C:32]([CH3:31])=[CH:33][CH:34]=3)[C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([C:19]([N:21]2[CH2:22][CH2:23][N:24]([CH:27]([CH3:28])[CH3:29])[CH2:25][CH2:26]2)=[O:20])=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 79799Tolylboronic acidHCID 68680853(4,4-Difluoro-piperidin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone

Product 1

HCID 68682179HCID 68682179, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

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), 146 mg (1.1 mmol) 4-methylphenylboronic acid, 0.13 g (0.72 mmol) copper(II) acetate and 0.12 mL (0.11 g, 1.43 mmol) pyridine in 5 mL dichloromethane was stirred for 3 days at room temperature. 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 89 mg (49%) of the desired compound as a colorless foam.

Workup

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

Sources & evidence

ORD record
ord-19e56eb78c424f78810aa6d8e0fd0fb0
Source dataset
uspto-grants-2010_05
Patent number
US07723325B2

Reaction notes

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