2-Dimethylamino-4-hydroxymethyl-3,5,6-trifluoropyridine → (2-Dimethylamino-3,5,6-trifluoropyridin-4-YL)methyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 256164Notes

Reaction equation

HRID 256164 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]1[C:8]([F:9])=[C:7]([CH2:10][OH:11])[C:6]([F:12])=[C:5]([F:13])[N:4]=1.[Cl:15][C:16]([C:26]([F:29])([F:28])[F:27])=[CH:17][C@@H:18]1[C@H:20]([C:21](Cl)=[O:22])[C:19]1([CH3:25])[CH3:24]>>[Cl:15][C:16]([C:26]([F:27])([F:28])[F:29])=[CH:17][C@@H:18]1[C@H:20]([C:21]([O:11][CH2:10][C:7]2[C:6]([F:12])=[C:5]([F:13])[N:4]=[C:3]([N:2]([CH3:14])[CH3:1])[C:8]=2[F:9])=[O:22])[C:19]1([CH3:25])[CH3:24]

Participants

3

Reactant 2

HCID 139851642-Dimethylamino-4-hydroxymethyl-3,5,6-trifluoropyridineHCID 86737382cis-3-(2-Chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarbonyl chloride

Product 1

HCID 86741837(2-Dimethylamino-3,5,6-trifluoropyridin-4-YL)methyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate

Procedure

By the method of Example 2, 0.5 g (0.002 mole) of 2-dimethylamino-4-hydroxymethyl-3,5,6-trifluoropyridine (from Example 13) was reacted with 0.6 g (0.002 mole) of cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarbonyl chloride to produce, after purification through a short silica gel column and the Chromatotron, 0.45 g of (2-methoxy-3,5,6-trifluoropyridin-4-yl)methyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate as an oil, Compound No. 20 of the tables below.

Workup

  1. customto produce
  2. customafter purification through a short silica gel column

Sources & evidence

ORD record
ord-d7ab4745f946446ca810abbe7571624c
Source dataset
uspto-grants-1987_10
Patent number
US04701464

Reaction notes

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