(4,5-Difluoro-2-methoxyphenyl)boronic acid → [4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-ylamino]-acetic acid methyl ester

HRID 878196Notes

Reaction equation

HRID 878196 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[C:20]([F:21])=[CH:19][C:18](B(O)O)=[C:17]([O:25][CH3:26])[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]=[C:20]([F:21])[C:15]([F:14])=[CH:16][C:17]=1[O:25][CH3:26]

Participants

4

Reactant 2

HCID 16217679(4,5-Difluoro-2-methoxyphenyl)boronic acidHCID 70663232(4-Iodo-pyridin-3-ylamino)-acetic acid methyl ester

Product 1

HCID 70663491[4-(4,5-Difluoro-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 4,5-difluoro-2-methoxyphenylboronic acid (CAS RN 870777-32-5) and using a gradient of n-heptane:EtOAc (100:0 to 0:100) for the chromatographic purification. Light yellow oil (82%). MS (ESI): m/z=309.104 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-3a3bac8c16a34568bdc6dba95f71feb3
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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