(4,5-Difluoro-2-methoxyphenyl)boronic acid → (2,2-Difluoro-ethyl)-[4-(4,5-difluoro-2-methoxy-phenyl)-pyridin-3-yl]-amine

HRID 878165Notes

Reaction equation

HRID 878165 reaction equation
[F:1][CH:2]([F:36])[CH2:3][N:4]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][C:26]=1[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=1[O:34][CH3:35])C(=O)C1C=C(C(F)(F)F)N=C(C(F)(F)F)C=1.[F:37]C1C(F)=CC(B(O)O)=C(OC)C=1>CCCCCCC.CCOC(C)=O>[F:1][CH:2]([F:36])[CH2:3][NH:4][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][C:26]=1[C:27]1[CH:32]=[C:31]([F:37])[C:30]([F:33])=[CH:29][C:28]=1[O:34][CH3:35]

Participants

4

Reactant 2

HCID 16217679(4,5-Difluoro-2-methoxyphenyl)boronic acidHCID 60198028HCID 60198028, compound2×

Product 1

HCID 86670766(2,2-Difluoro-ethyl)-[4-(4,5-difluoro-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 (example 153, intermediate b) and 4,5-difluoro-2-methoxyphenylboronic acid (CAS RN 870777-32-5) and using a gradient of n-heptane:EtOAc (100:0 to 50:50) for the chromatographic purification. Light brown solid (73%). MS (ESI): m/z=301.10 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-cb6512fb2b724d10a1e9748486754ee4
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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