(4-Fluoro-2-methoxyphenyl)boronic acid → (2,2-Difluoro-ethyl)-[4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]amine

HRID 878163Notes

Reaction equation

HRID 878163 reaction equation
[F:1][CH:2]([F:12])[CH2:3][NH:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1I.[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[C:16]([O:23][CH3:24])[CH:15]=1>CCCCCCC.CCOC(C)=O>[F:1][CH:2]([F:12])[CH2:3][NH:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[C:17]1[CH:18]=[CH:19][C:14]([F:13])=[CH:15][C:16]=1[O:23][CH3:24]

Participants

4

Reactant 2

HCID 2782672(4-Fluoro-2-methoxyphenyl)boronic acidHCID 866707643-Pyridinamine, N-(2,2-difluoroethyl)-4-iodo-

Product 1

HCID 86670763(2,2-Difluoro-ethyl)-[4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]amine

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 72, from (2,2-difluoro-ethyl)-(4-iodo-pyridin-3-yl)-amine and 4-fluoro-2-methoxyphenylboronic acid (CAS RN 179899-07-1) and using a gradient of n-heptane:EtOAc (100:0 to 50:50) for the chromatographic purification. Light brown solid (78%). MS (ESI): m/z=283.18 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-6a88efdb49f940438b758a7d36dd22e4
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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