5-Fluoro-2-methylphenylboronic acid → 6-chloro-4-(5-fluoro-2-methylphenyl)-N-methylpyridin-3-amine

HRID 878290Notes

Reaction equation

HRID 878290 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:13]=[CH:14][C:15]([CH3:21])=[C:16](B(O)O)[CH:17]=1>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH3:9])=[C:4]([C:14]2[CH:13]=[C:12]([F:11])[CH:17]=[CH:16][C:15]=2[CH3:21])[CH:3]=1

Participants

3

Reactant 2

HCID 27831905-Fluoro-2-methylphenylboronic acidHCID 574434006-Chloro-4-iodo-N-methylpyridin-3-amine

Product 1

HCID 577104506-chloro-4-(5-fluoro-2-methylphenyl)-N-methylpyridin-3-amine

Procedure

The title compound was prepared in analogy to example 72, from 6-chloro-4-iodo-N-methylpyridin-3-amine (prepared according to WO2006013050) and 5-fluoro-2-methylphenylboronic acid after heating at reflux for 21 hours. The compound was purified by silica gel chromatography on a 50 g column using an MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 50:50). Light brown solid (85%). MS (ESI): m/z=251.08 [M+H]+.

Workup

  1. temperatureafter heating
  2. temperatureat reflux for 21 hours
  3. customThe compound was purified by silica gel chromatography on a 50 g column
  4. washeluting with a gradient of n-heptane:EtOAc (100:0 to 50:50)

Sources & evidence

ORD record
ord-8a33777f3ae042c4b4ae8e72cd139589
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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