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

HRID 878169Notes

Reaction equation

HRID 878169 reaction equation
[F:1][CH:2]([F:36])[CH2:3][N:4]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][C:26]=1[C:27]1[CH:32]=[CH:31][C:30](F)=C[C:28]=1[O:34][CH3:35])C(=O)C1C=C(C(F)(F)F)N=C(C(F)(F)F)C=1.COC1C(B(O)O)=CC=C[N:40]=1>CCCCCCC.CCOC(C)=O>[F:1][CH:2]([F:36])[CH2:3][NH:4][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][C:26]=1[C:27]1[C:28]([O:34][CH3:35])=[N:40][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 60198028HCID 60198028, compound2×

Product 1

HCID 86670768(2,2-Difluoro-ethyl)-(2-methoxy-[3,4]bipyridinyl-3'-yl)-amine

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 72, from (2,2-difluoro-ethyl)-(4-iodo-pyridin-3-yl)-amine (example 153, intermediate b) and 2-methoxypyridine-3-boronic acid (CAS RN 163105-90-6) and using a gradient of n-heptane:EtOAc (100:0 to 50:50) for the chromatographic purification. Colorless solid (83%). MS (ESI): m/z=266.11 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-cb229144b5c64a4ebd6940f85caac8d1
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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