(2-(2,2,2-Trifluoroethoxy)pyridin-3-yl)boronic acid → Methyl-[2-(2,2,2-trifluoro-ethoxy)-[3,4]bipyridinyl-3'-yl]-amine

HRID 878319Notes

Reaction equation

HRID 878319 reaction equation
FC1C(F)=CC([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:15](CCS(C)(=O)=O)[C:16](=O)C2C=C(C(F)(F)F)N=C(C(F)(F)F)C=2)=C(OC)C=1.[F:40][C:41]([F:54])([F:53])[CH2:42][O:43][C:44]1[C:49](B(O)O)=[CH:48][CH:47]=[CH:46][N:45]=1>>[CH3:16][NH:15][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:9]=1[C:49]1[C:44]([O:43][CH2:42][C:41]([F:54])([F:53])[F:40])=[N:45][CH:46]=[CH:47][CH:48]=1

Participants

3

Reactant 2

HCID 53216590(2-(2,2,2-Trifluoroethoxy)pyridin-3-yl)boronic acidHCID 86670771N-[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-(2-methanesulfonyl-ethyl)-2,6-bis-trifluoromethyl-isonicotinamide2×

Product 1

HCID 70663341Methyl-[2-(2,2,2-trifluoro-ethoxy)-[3,4]bipyridinyl-3'-yl]-amine

Procedure

The title compound was prepared in analogy to example 72, from 4-iodo-N-methylpyridin-3-amine (example 98, intermediate b) and 2-(2,2,2-trifluoroethoxy)pyridin-3-ylboronic acid after a reaction time of 5 hours at 90° C. The compound was purified by silica gel chromatography on a 10 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless oil (76%). MS (ESI): m/z=284.10 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 10 g column
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-12971b6546ac4343bc457a19e8db18b8
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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