(2-Methoxypyridin-3-yl)boronic acid → (2-Methanesulfonyl-ethyl)-(2-methoxy-[3,4']bipyridinyl-3'-yl)-amine

HRID 878177Notes

Reaction equation

HRID 878177 reaction equation
F[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])C=1.COC1C(B(O)O)=CC=C[N:43]=1>C(Cl)Cl.CO>[CH3:37][S:34]([CH2:33][CH2:32][NH:15][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:9]=1[C:5]1[C:4]([O:38][CH3:39])=[N:43][CH:2]=[CH:7][CH:6]=1)(=[O:36])=[O:35]

Participants

4

Reactant 2

HCID 2762709(2-Methoxypyridin-3-yl)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 70663393(2-Methanesulfonyl-ethyl)-(2-methoxy-[3,4']bipyridinyl-3'-yl)-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 2-methoxypyridine-3-boronic acid (CAS RN 163105-90-6) and using a gradient of CH2Cl2:methanol (100:0 to 85:15) for the chromatographic purification. Brown solid (89%). MS (ESI): m/z=308.11 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-fd624e963e514c5e9e92cf71cc3ea1e3
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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