(2-Chloropyridin-3-yl)boronic acid → 2-chloro-N-methyl-3,4'-bipyridin-3'-amine

HRID 878369Notes

Reaction equation

HRID 878369 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][CH3:9].[Cl:10][C:11]1[C:16](B(O)O)=[CH:15][CH:14]=[CH:13][N:12]=1>>[Cl:10][C:11]1[C:16]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[NH:8][CH3:9])=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

3

Reactant 2

HCID 2762704(2-Chloropyridin-3-yl)boronic acidHCID 706632374-iodo-N-methylpyridin-3-amine

Product 1

HCID 866708262-chloro-N-methyl-3,4'-bipyridin-3'-amine

Procedure

The title compound was prepared in analogy to example 72, from (4-iodo-pyridin-3-yl)-methyl-amine and 2-chloropyridin-3-ylboronic acid after a reaction time of 5 hours at 90° C. The compound was purified by silica gel chromatography on a 50 g column using an MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Light yellow solid (82%). MS (EI): m/z=219 [M]+.

Workup

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

Sources & evidence

ORD record
ord-0eac17388f6e43f7a42aaa4aa2059dad
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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