Water → Methyl 4-(4-methoxyphenylamino)-5-fluoro-6-(4-chlorophenyl)picolinate

HRID 1774283Notes

Reaction equation

F[C:2]([F:20])(F)[C:3](=[N:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[C:4]#[C:5][C:6]([O:8][CH3:9])=[O:7].[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCCC1>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:3]2[C:2]([F:20])=[C:26]([C:25]3[CH:28]=[CH:29][C:22]([Cl:21])=[CH:23][CH:24]=3)[N:27]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In a typical reaction, methyl 5,5,5-trifluoro-4-((4-methoxyphenyl)imino)pent-2-ynoate is mixed with about a 2.5 to 3 fold excess of 4-chlorobenzyl amine and about a 2.5 to 3 fold excess of cesium carbonate in anhydrous terahydrofuran. The mixture is heated at about 80° C. until the reaction is complete. After cooling, an extraction solvent like a halogenated hydrocarbon is added to the mixture along with water. The organic layer is recovered, washed with brine and dried. The solvent is evaporated to provide crude methyl 4-(4-methoxyphenylamino)-5-fluoro-6-(4-chlorophenyl)picolinate.

Workup

temperatureAfter cooling
customThe organic layer is recovered
washwashed with brine
customdried
customThe solvent is evaporated

Sources & evidence

ORD record: ord-42ca26dd47d4421bb29c66756e311409
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260392B2

Reaction notes

Loading…