3-(4-Bromo-3-methylphenyl)-5-methyl-1,2,4-oxadiazole → 6,2'-Dimethyl-4'-(5-methyl-[1,2,4]oxadiazol-3-yl)-biphenyl-3-carboxylic acid (3-morpholin-4-yl-phenyl)amide

HRID 31459

Reaction equation

HRID 31459 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH3:13])[O:10][N:9]=2)=[CH:4][C:3]=1[CH3:14].[CH3:15][C:16]1[CH:36]=[CH:35][C:19]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[CH:24]=2)=[O:21])=[CH:18][C:17]=1B1OC(C)(C)C(C)(C)O1>CC(O)C>[N:29]1([C:25]2[CH:24]=[C:23]([NH:22][C:20]([C:19]3[CH:35]=[C:36]([C:2]4[CH:7]=[CH:6][C:5]([C:8]5[N:12]=[C:11]([CH3:13])[O:10][N:9]=5)=[CH:4][C:3]=4[CH3:14])[C:16]([CH3:15])=[CH:17][CH:18]=3)=[O:21])[CH:28]=[CH:27][CH:26]=2)[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1

Participants

4

Reactant 2

HCID 121219443-(4-Bromo-3-methylphenyl)-5-methyl-1,2,4-oxadiazoleHCID 597915214-methyl-N-[3-(4-morpholinyl)phenyl]-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzamide2×

Product 1

HCID 586298006,2'-Dimethyl-4'-(5-methyl-[1,2,4]oxadiazol-3-yl)-biphenyl-3-carboxylic acid (3-morpholin-4-yl-phenyl)amide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Example 32 was prepared using 3-(4-bromo-3-methylphenyl)-5-methyl-[1,2,4]oxadiazole and 4-methyl-N-(3-morpholin-4-yl-phenyl)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl) -benzamide (Intermediate 5) with propan-2-ol as the solvent.

Workup

  1. customExample 32 was prepared

Sources & evidence

ORD record
ord-8c84d73a086a41d6ade84a5fde6de898
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Linked notes

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