Sodium Carbonate → N-cyclopropyl-6-methyl-4'-[5-(methylamino)-1,3,4-oxadiazol-2-yl]-1,1'-biphenyl-3-carboxamide

HRID 31472Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([NH:13][CH3:14])=[N:11][N:12]=2)=[CH:4][CH:3]=1.[CH:15]1([NH:18][C:19](=[O:36])[C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[C:22](B3OC(C)(C)C(C)(C)O3)[CH:21]=2)[CH2:17][CH2:16]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:15]1([NH:18][C:19]([C:20]2[CH:25]=[C:24]([C:2]3[CH:7]=[CH:6][C:5]([C:8]4[O:9][C:10]([NH:13][CH3:14])=[N:11][N:12]=4)=[CH:4][CH:3]=3)[C:23]([CH3:26])=[CH:22][CH:21]=2)=[O:36])[CH2:16][CH2:17]1

Participants

Conditions

Temperature: 80 °C

Procedure

2-(4-Iodophenyl)-5-(methylamino)-1,3,4-oxadiazole (Intermediate 36) (30 mg), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (33 mg), tetrakis(triphenylphosphine)palladium (13 mg) and aqueous sodium carbonate (1M, 0.11 ml) in DME (3 ml) were mixed and heated at 80° C. for 18 hours. The reaction was purified by HPLC to give N-cyclopropyl-6-methyl-4′-[5-(methylamino)-1,3,4-oxadiazol-2-yl]-1,1′-biphenyl-3-carboxamide.

Workup

customThe reaction was purified by HPLC

Sources & evidence

ORD record: ord-5eaba3c502644856ae0c279a2cc9e814
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425555B2

Reaction notes

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