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

HRID 31473Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:13]3[N:14]([CH3:18])[CH:15]=[CH:16][CH:17]=3)=[N:11][N:12]=2)=[CH:4][CH:3]=1.[CH:19]1([NH:22][C:23](=[O:40])[C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26](B3OC(C)(C)C(C)(C)O3)[CH:25]=2)[CH2:21][CH2:20]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:19]1([NH:22][C:23]([C:24]2[CH:29]=[C:28]([C:2]3[CH:7]=[CH:6][C:5]([C:8]4[O:9][C:10]([C:13]5[N:14]([CH3:18])[CH:15]=[CH:16][CH:17]=5)=[N:11][N:12]=4)=[CH:4][CH:3]=3)[C:27]([CH3:30])=[CH:26][CH:25]=2)=[O:40])[CH2:20][CH2:21]1

Participants

Conditions

Temperature: 80 °C

Procedure

2-(4-Iodophenyl)-5-(1-methyl-1H-pyrrol-2-yl)-1,3,4-oxadiazole (intermediate 38) (35 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 bond-elut (silica), eluting with an ethyl acetate/cyclohexane gradient to give, after evaporation of the solvent, N-cyclopropyl-6-methyl-4′-[5-(1-methyl-1H-pyrrol-2-yl)-1,3,4-oxadiazol-2-yl]-1,1′-biphenyl-3-carboxamide.

Workup

customThe reaction was purified by bond-elut (silica)
washeluting with an ethyl acetate/cyclohexane gradient
customto give
customafter evaporation of the solvent, N-cyclopropyl-6-methyl-4′-[5-(1-methyl-1H-pyrrol-2-yl)-1,3,4-oxadiazol-2-yl]-1,1′-biphenyl-3-carboxamide

Sources & evidence

ORD record: ord-bd954781e6ea4c05b85d3d04e01b2b0c
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425555B2

Reaction notes

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