(2-(2,2,2-Trifluoroethoxy)pyridin-3-yl)boronic acid → N-Methyl-N-[2-(2,2,2-trifluoro-ethoxy)-[3,4']bipyridinyl-3'-yl]-3,5-bis-trifluoromethyl-benzamide

HRID 878101Notes

Reaction equation

HRID 878101 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]([CH3:25])[C:9](=[O:24])[C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1.[F:26][C:27]([F:40])([F:39])[CH2:28][O:29][C:30]1[C:35](B(O)O)=[CH:34][CH:33]=[CH:32][N:31]=1>CCCCCCC.CCOC(C)=O>[CH3:25][N:8]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[C:35]1[C:30]([O:29][CH2:28][C:27]([F:39])([F:26])[F:40])=[N:31][CH:32]=[CH:33][CH:34]=1)[C:9](=[O:24])[C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1

Participants

4

Reactant 2

HCID 53216590(2-(2,2,2-Trifluoroethoxy)pyridin-3-yl)boronic acidHCID 86670697N-(4-iodopyridin-3-yl)-N-methyl-3,5-bis(trifluoromethyl)benzamide

Product 1

HCID 86670728N-Methyl-N-[2-(2,2,2-trifluoro-ethoxy)-[3,4']bipyridinyl-3'-yl]-3,5-bis-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 72, from N-(4-iodo-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide (example 98, intermediate a) and 2-(2,2,2-trifluoroethoxy)pyridin-3-ylboronic acid (Combi-Blocks Inc.) and using a gradient of n-heptane:EtOAc (100:0 to 30:70) for the chromatographic purification. Colorless solid (58%). MS (ESI): m/z=524.103 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-0c67abd07d4d41f9a397b8ed7f6811f7
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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