2,6-Difluoro-3-methoxybenzeneboronic acid → [4-(2,6-Difluoro-3-methoxy-phenyl)-pyridin-3-yl]-methyl-amine

HRID 878325Notes

Reaction equation

HRID 878325 reaction equation
COC1N=C([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:15](C)[C:16](=O)C2C=C(C(F)(F)F)C=C(C(F)(F)F)C=2)C=CC=1.[F:33][C:34]1[C:39]([O:40][CH3:41])=[CH:38][CH:37]=[C:36]([F:42])[C:35]=1B(O)O>CCCCCC.CCOC(C)=O>[F:33][C:34]1[C:39]([O:40][CH3:41])=[CH:38][CH:37]=[C:36]([F:42])[C:35]=1[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[NH:15][CH3:16]

Participants

4

Reactant 2

HCID 27831312,6-Difluoro-3-methoxybenzeneboronic acidHCID 60196806HCID 60196806, compound

Product 1

HCID 70663575[4-(2,6-Difluoro-3-methoxy-phenyl)-pyridin-3-yl]-methyl-amine

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The title compound was prepared in analogy to compound 284, intermediate, from (4-iodo-pyridin-3-yl)-methyl-amine (example 98, intermediate) and 2,6-difluoro-3-methoxyphenylboronic acid and using a gradient of n-hexane:EtOAc (70:30 to 60:40) for the chromatographic purification. Brown solid (75%). MS (ESI): m/z=251.2 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-4f5d57f48af24ae18c882602ee18fb9d
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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