(4-Fluoro-2-methoxyphenyl)boronic acid → 4-(4-fluoro-2-methoxyphenyl)-N-(2-(methylsulfonyl)ethyl)pyridin-3-amine

HRID 878181Notes

Reaction equation

HRID 878181 reaction equation
[F:1][C:2]1[C:7](F)=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:15]([CH2:32][CH2:33][S:34]([CH3:37])(=[O:36])=[O:35])C(=O)C2C=C(C(F)(F)F)N=C(C(F)(F)F)C=2)=[C:4]([O:38][CH3:39])[CH:3]=1.FC1C=CC(B(O)O)=C(OC)C=1>C(Cl)Cl.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[NH:15][CH2:32][CH2:33][S:34]([CH3:37])(=[O:35])=[O:36])=[C:4]([O:38][CH3:39])[CH:3]=1

Participants

4

Reactant 2

HCID 2782672(4-Fluoro-2-methoxyphenyl)boronic acidHCID 86670771N-[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-(2-methanesulfonyl-ethyl)-2,6-bis-trifluoromethyl-isonicotinamide2×

Product 1

HCID 706632644-(4-fluoro-2-methoxyphenyl)-N-(2-(methylsulfonyl)ethyl)pyridin-3-amine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared in analogy to example 72, from (4-iodo-pyridin-3-yl)-(2-methanesulfonyl-ethyl)-amine (example 158, intermediate b) and 4-fluoro-2-methoxyphenyl-boronic acid (CAS RN 179899-07-1) and using a gradient of CH2Cl2:methanol (100:0 to 85:15) for the chromatographic purification. Colorless foam (55%). MS (ESI): m/z=325.10 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-f89dc218b1bc48c596d386d96ac6305a
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…