2-Chlorophenylboronic acid → 4-(2-chlorophenyl)-6-methyl-N-(2,2,2-trifluoroethyl)pyridin-3-amine

HRID 878345Notes

Reaction equation

HRID 878345 reaction equation
I[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[CH:4][C:3]=1[NH:9][CH2:10][C:11]([F:14])([F:13])[F:12].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O>>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[CH:4][C:3]=1[NH:9][CH2:10][C:11]([F:14])([F:13])[F:12]

Participants

3

Reactant 2

HCID 27343222-Chlorophenylboronic acidHCID 706631914-iodo-6-methyl-N-(2,2,2-trifluoroethyl)pyridin-3-amine

Product 1

HCID 706635194-(2-chlorophenyl)-6-methyl-N-(2,2,2-trifluoroethyl)pyridin-3-amine

Procedure

The title compound was prepared in analogy to example 72, from 4-iodo-6-methyl-N-(2,2,2-trifluoroethyl)pyridin-3-amine and 2-chlorophenylboronic acid after a reaction time of 15.5 hours. 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 50:50). Light brown solid (71%). MS (ESI): m/z=301.07 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 10 g column
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 50:50)

Sources & evidence

ORD record
ord-753f298cf3e44d419b8fd45676ea3d5e
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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