(4-Fluoro-2-methoxyphenyl)boronic acid → [2-Chloro-4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-methyl-amine

HRID 878241Notes

Reaction equation

HRID 878241 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][CH3:9])=[C:6](I)[CH:5]=[CH:4][N:3]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[C:14]([O:21][CH3:22])[CH:13]=1>>[Cl:1][C:2]1[C:7]([NH:8][CH3:9])=[C:6]([C:15]2[CH:16]=[CH:17][C:12]([F:11])=[CH:13][C:14]=2[O:21][CH3:22])[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 2782672(4-Fluoro-2-methoxyphenyl)boronic acidHCID 86670801(2-Chloro-4-iodo-pyridin-3-yl)-methyl-amine

Product 1

HCID 86670800[2-Chloro-4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-methyl-amine

Procedure

The title compound was prepared in analogy to example 72, from (2-chloro-4-iodo-pyridin-3-yl)-methyl-amine and 4-fluoro-2-methoxyphenylboronic acid (CAS RN 179899-07-1). The compound was purified by silica gel chromatography on a 20 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 60:40). Light yellow solid (78%). MS (ESI): m/z=267.07 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 20 g column
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 60:40)

Sources & evidence

ORD record
ord-1cc7401539624cf8ba3888007d989f82
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…