(4-Fluoro-2-methoxyphenyl)boronic acid → [6-Chloro-4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-methyl-amine

HRID 878223Notes

Reaction equation

HRID 878223 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH3:9])=[C:4](I)[CH:3]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[C:14]([O:21][CH3:22])[CH:13]=1>CCCCCCC.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH3:9])=[C:4]([C:15]2[CH:16]=[CH:17][C:12]([F:11])=[CH:13][C:14]=2[O:21][CH3:22])[CH:3]=1

Participants

4

Reactant 2

HCID 2782672(4-Fluoro-2-methoxyphenyl)boronic acidHCID 574434006-chloro-4-iodo-N-methylpyridin-3-amine

Product 1

HCID 86670794[6-Chloro-4-(4-fluoro-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 (6-chloro-4-iodo-pyridin-3-yl)-methyl-amine (prepared according to WO2006013050) 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. Off-white solid (81%). MS (ESI): m/z=267.07 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-931e822e52954991b50c99870a8dcebe
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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