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

HRID 878136Notes

Reaction equation

HRID 878136 reaction equation
C[N:2]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1N1CCCCC1C)[C:3](=O)C1C=C(C(F)(F)F)C=C(C(F)(F)F)C=1.[F:32][C:33]1[C:38]([F:39])=[CH:37][C:36](B(O)O)=[C:35]([O:43][CH3:44])[CH:34]=1>CCCCCCC.CCOC(C)=O>[F:32][C:33]1[C:38]([F:39])=[CH:37][C:36]([C:24]2[CH:23]=[CH:22][N:21]=[CH:20][C:19]=2[NH:2][CH3:3])=[C:35]([O:43][CH3:44])[CH:34]=1

Participants

4

Reactant 2

HCID 16217679(4,5-Difluoro-2-methoxyphenyl)boronic acidHCID 86670691N-Methyl-N-(2-methyl-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-3'-yl)-3,5-bis-trifluoromethyl-benzamide2×

Product 1

HCID 70663277[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-methyl-amine

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 72, from (4-iodo-pyridin-3-yl)-methyl-amine (example 98, 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 separation. Light brown solid (91%). MS (ESI): m/z=251.099 [M+H]+.

Workup

  1. customfor the chromatographic separation

Sources & evidence

ORD record
ord-6a317d13bc4f49ae825694ead9d3cd9d
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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