(2-Methoxypyridin-3-yl)boronic acid → Methyl 2-(4-(2-methoxypyridin-3-yl)pyridin-3-ylamino)acetate

HRID 878203Notes

Reaction equation

HRID 878203 reaction equation
FC1C(F)=CC([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:15](CCS(C)(=O)=O)C(=O)C2C=C(C(F)(F)F)N=C(C(F)(F)F)C=2)=C(OC)C=1.[CH3:40][O:41][C:42]1[C:47](B(O)O)=[CH:46][CH:45]=[CH:44][N:43]=1.CCCCCCC.C[CH2:59][O:60][C:61]([CH3:63])=[O:62]>>[CH3:59][O:60][C:61](=[O:62])[CH2:63][NH:15][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:9]=1[C:47]1[C:42]([O:41][CH3:40])=[N:43][CH:44]=[CH:45][CH:46]=1

Participants

4

Reactant 3

HCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 21899848Ethylacetate heptaneHCID 86670771N-[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-(2-methanesulfonyl-ethyl)-2,6-bis-trifluoromethyl-isonicotinamide2×

Product 1

HCID 70663573Methyl 2-(4-(2-methoxypyridin-3-yl)pyridin-3-ylamino)acetate

Procedure

The title compound was prepared in analogy to example 72, from (4-iodo-pyridin-3-ylamino)-acetic acid methyl ester (example 176, intermediate b) and 2-methoxypyridine-3-boronic acid (CAS RN 163105-90-6) and using a gradient of n-heptane:EtOAc (100:0 to 0:100) for the chromatographic purification. Light yellow oil (73%). MS (ESI): m/z=274.119 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-e583ce4460704828a7d0fa1f0606b8da
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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