(4-Fluoro-2-methoxyphenyl)boronic acid → 4-(4-fluoro-2-methoxyphenyl)-N,6-dimethylpyridin-3-amine

HRID 878349Notes

Reaction equation

HRID 878349 reaction equation
I[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[CH:4][C:3]=1[NH:9][CH3:10].[F:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[C:14]([O:21][CH3:22])[CH:13]=1>>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:7]=[C:6]([CH3:8])[N:5]=[CH:4][C:3]=2[NH:9][CH3:10])=[C:14]([O:21][CH3:22])[CH:13]=1

Participants

3

Reactant 2

HCID 2782672(4-Fluoro-2-methoxyphenyl)boronic acidHCID 70663536(4-Iodo-6-methyl-pyridin-3-yl)-methyl-amine

Product 1

HCID 706636684-(4-fluoro-2-methoxyphenyl)-N,6-dimethylpyridin-3-amine

Procedure

The title compound was prepared in analogy to example 72, from (4-iodo-6-methyl-pyridin-3-yl)-methyl-amine and 4-fluoro-2-methoxyphenylboronic acid after a reaction time of 14.5 hours at reflux. The compound was purified by silica gel chromatography on a 10 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Light brown solid (84%). MS (ESI): m/z=247.12 [M+H]+.

Workup

  1. temperatureat reflux
  2. customThe compound was purified by silica gel chromatography on a 10 g column
  3. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-d2ccbf458ed240128c0092f21ebdabd1
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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