Water → HCID 86723379, compound

HRID 508539Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:32][CH2:33][CH3:34])[C:5]#[C:6][C:7](=[N:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8](F)(F)[F:9])[CH3:2].[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][NH2:43])=[C:38]([F:44])[C:37]=1[O:45][CH3:46].C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCCC1>[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[C:8]([F:9])=[C:7]([NH:12][C:13]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:6]=[C:5]([CH:4]([O:3][CH2:1][CH3:2])[O:32][CH2:33][CH3:34])[N:43]=2)=[C:38]([F:44])[C:37]=1[O:45][CH3:46]

Participants

Conditions

Temperature: 80 °C

Procedure

In a typical reaction, N-(5,5-diethoxy-1,1,1-trifluoropent-3-yn-2-ylidene)-1,1,1-triphenylmethanamine is mixed with about a 2.5 to 3 fold excess of (4-chloro-2-fluoro-3-methoxyphenyl)methyl 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 2-(4-chloro-2-fluoro-3-methoxyphenyl)-6-(diethoxymethyl)-3-fluoro-N-tritylpyridin-4-amine.

Workup

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

Sources & evidence

ORD record: ord-e62364366466485cb98a867cc456d420
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096526B2

Reaction notes

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