(4-Fluoro-2-methoxyphenyl)boronic acid → [4-(4-Fluoro-2-methoxy-phenyl)-pyridin-3-ylamino]-acetic acid methyl ester

HRID 878201Notes

Reaction equation

HRID 878201 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][NH:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1I.[F:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[C:17]([O:24][CH3:25])[CH:16]=1>CCCCCCC.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:13])[CH2:4][NH:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[C:18]1[CH:19]=[CH:20][C:15]([F:14])=[CH:16][C:17]=1[O:24][CH3:25]

Participants

4

Reactant 2

HCID 2782672(4-Fluoro-2-methoxyphenyl)boronic acidHCID 70663232(4-Iodo-pyridin-3-ylamino)-acetic acid methyl ester

Product 1

HCID 70663553[4-(4-Fluoro-2-methoxy-phenyl)-pyridin-3-ylamino]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 72, from (4-iodo-pyridin-3-ylamino)-acetic acid methyl ester and 4-fluoro-2-methoxyphenylboronic acid (CAS RN 179899-07-1) 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=291.113 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-b045f1a08b0541e9a465b30fa849819f
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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