Pyridine → HCID 68535708, compound

HRID 1992457Notes

Reaction equation

HRID 1992457 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([C:21]([N:23]2[CH2:28][CH2:27][N:26]([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:25][CH2:24]2)=[O:22])=[CH:15]3)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[Cl:33][C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][CH:39]=1.N1C=CC=CC=1>C(Cl)(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:33][C:34]1[CH:39]=[C:38]([N:17]2[C:18]3[C:14](=[CH:13][C:12]([C:10]([N:7]4[CH2:8][CH2:9][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6]4)=[O:11])=[CH:20][CH:19]=3)[CH:15]=[C:16]2[C:21]([N:23]2[CH2:24][CH2:25][N:26]([S:29]([CH3:32])(=[O:30])=[O:31])[CH2:27][CH2:28]2)=[O:22])[CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 2734323(3-Chlorophenyl)boronic acidHCID 68538245[5-(4-Isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanone

Product 1

HCID 68535708HCID 68535708, compoundYield 42.7%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6212ChloroformSolvent

Procedure

A suspension of 0.20 g (0.43 mmol) [5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanone (example 1), 0.20 g (1.30 mmol) 3-chlorophenylboronic acid, 0.16 g (0.86 mmol) copper(II) acetate and 0.14 mL (0.14 g, 1.73 mmol) pyridine in 5 mL chloroform was stirred 4.5 days at room temperature. The volatile components were evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel with a gradient of dichloromethane:methanol (100:0 to 75:25 v/v) as eluant to afford 105 mg (42%) of the desired compound as a light-brown foam. MS (ISP): 572.2 (M+H)+.

Workup

  1. customThe volatile components were evaporated under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel with a gradient of dichloromethane:methanol (100:0 to 75:25 v/v) as eluant

Sources & evidence

ORD record
ord-27ac3c219cf540648c277bf678615ab3
Source dataset
uspto-grants-2010_01
Patent number
US07648979B2

Reaction notes

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