3-(4-Bromophenyl)-5-methyl-1,2,4-oxadiazole → N-[6-Methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-3-yl]-2-(1-pyrrolidinyl)-4-pyridinecarboxamide

HRID 31440Notes

Reaction equation

HRID 31440 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][CH:3]=1.[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[CH:25]=2)=[O:23])=[CH:17][C:16]=1B1OC(C)(C)C(C)(C)O1>>[CH3:14][C:15]1[C:20]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:12]=[C:11]([CH3:13])[O:10][N:9]=3)=[CH:4][CH:3]=2)=[CH:19][C:18]([NH:21][C:22]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[CH:25]=2)=[O:23])=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 8235603-(4-Bromophenyl)-5-methyl-1,2,4-oxadiazoleHCID 11258289N-[4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-2-pyrrolidin-1-yl-isonicotinamide2×

Product 1

HCID 44580360N-[6-Methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-3-yl]-2-(1-pyrrolidinyl)-4-pyridinecarboxamide

Procedure

Example 11 was prepared using 3-(4-bromophenyl)-5-methyl-1,2,4-oxadiazole and N-[4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]-2-(1-pyrrolidinyl)-4-pyridinecarboxamide (Intermediate 20).

Workup

  1. customExample 11 was prepared

Sources & evidence

ORD record
ord-f458f9c56f6b4dfd8d094d732d05d534
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Reaction notes

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