Water → 2-(4-chlorophenyl)-6-(diethoxymethyl)-3-fluoro-N-(4-methoxyphenyl)pyridin-4-amine

HRID 1503101Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:21][CH2:22][CH3:23])[C:5]#[C:6][C:7](=[N:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:8]([F:11])(F)F)[CH3:2].[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCCC1>[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([C:29]2[C:8]([F:11])=[C:7]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:6]=[C:5]([CH:4]([O:3][CH2:1][CH3:2])[O:21][CH2:22][CH3:23])[N:30]=2)=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In a typical reaction, N-(5,5-diethoxy-1,1,1-trifluoro-pent-3-yn-2-ylidene)-4-methoxyaniline is mixed with about a 2.5 to 3 fold excess of p-chlorobenzylamine and about a 2.5 to 3 fold excess of cesium carbonate in anhydrous tetrahydrofuran. 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 2-(4-chlorophenyl)-6-(diethoxymethyl)-3-fluoro-N-(4-methoxyphenyl)pyridin-4-amine.

Workup

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

Sources & evidence

ORD record: ord-a0f40bf42a7544b69f9f94d6932d43d7
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212141B2

Reaction notes

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