Sodium Bicarbonate → 1-(3-Cyclopropyl-5-trifluoromethylpyridin-2-yl)piperazine

HRID 2411220Notes

Reaction equation

HRID 2411220 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19](Cl)=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH:25]1(B(O)O)[CH2:27][CH2:26]1.C(=O)([O-])O.[Na+]>>[CH:25]1([C:19]2[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[N:15][CH:16]=[C:17]([C:21]([F:22])([F:23])[F:24])[CH:18]=2)[CH2:27][CH2:26]1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 2760897Cyclopropylboronic acidHCID 57366416HCID 57366416, compound

Product 1

HCID 584847721-(3-Cyclopropyl-5-trifluoromethylpyridin-2-yl)piperazineYield 83.3%

Procedure

To 1-(3-cyclopropyl-5-trifluoromethylpyridin-2-yl)piperazine hydrochloride obtained by using the intermediate 4-(3-chloro-5-trifluoromethylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (5.86 g) described in Preparation Example 84 and cyclopropylboronic acid (5 g) and by the reaction and treatment in the same manner as in Preparation Example 82 was added saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated to give the title compound (3.62 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-dfa0b4c75d5f4dfba5a8a0540c579335
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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