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

HRID 878218Notes

Reaction equation

HRID 878218 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.[F:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1B(O)O.CCCCCCC.C[CH2:58][O:59][C:60]([CH3:62])=[O:61]>>[CH3:58][O:59][C:60](=[O:61])[CH2:62][NH:15][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:9]=1[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=1[F:40]

Participants

4

Reactant 3

HCID 27343542-Fluorophenylboronic 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 70663196[4-(2-Fluoro-phenyl)-pyridin-3-ylamino]-acetic acid methyl ester

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-fluorophenylboronic acid (CAS RN 1193-03-9) and using a gradient of n-heptane:EtOAc (100:0 to 0:100) for the chromatographic purification. Off-white solid (37%). MS (ESI): m/z=261.104 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-5ad44ac94c374a79b0a42f978d5bc4fc
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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