5-(2,4-Bis(benzyloxy)-5-chlorophenyl)-4-bromo-N-ethylisoxazole-3-carboxamide → 5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-[3-(4-methyl-piperazin-1-yl)-phenyl]-isoxazole-3-carboxylic acid ethylamide

HRID 646477Notes

Reaction equation

HRID 646477 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[C:10](Br)=[C:9]([C:12]2[CH:17]=[C:16]([Cl:18])[C:15]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:14][C:13]=2[O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:8][N:7]=1)=[O:5])[CH3:2].[CH3:35][N:36]1[CH2:41][CH2:40][N:39]([C:42]2[CH:47]=[CH:46][CH:45]=[C:44](B3OC(C)(C)C(C)(C)O3)[CH:43]=2)[CH2:38][CH2:37]1>>[CH2:1]([NH:3][C:4]([C:6]1[C:10]([C:44]2[CH:45]=[CH:46][CH:47]=[C:42]([N:39]3[CH2:40][CH2:41][N:36]([CH3:35])[CH2:37][CH2:38]3)[CH:43]=2)=[C:9]([C:12]2[CH:17]=[C:16]([Cl:18])[C:15]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:14][C:13]=2[O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:8][N:7]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 247740425-(2,4-Bis(benzyloxy)-5-chlorophenyl)-4-bromo-N-ethylisoxazole-3-carboxamideHCID 592647461-Methyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)piperazine

Product 1

HCID 592647295-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-[3-(4-methyl-piperazin-1-yl)-phenyl]-isoxazole-3-carboxylic acid ethylamideYield 83%

Procedure

5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-bromo-isoxazole-3-carboxylic acid ethylamide (38 mg, 0.07 mmol) and 1-Methyl-4-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-piperazine (31 mg, 2 equiv.) were coupled together using the suzuki method previously described to provide 37 mg (83% yield) of the crude as a brown oil which was taken on to the deprotection step.

Workup

  1. customto provide 37 mg (83% yield) of the crude as a brown oil which

Sources & evidence

ORD record
ord-685785b15c1246f8b6f6f550f3e2ecf9
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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