Reaction #1810823

ord-e59ba8f944534bc182c9ff8f6ed4ff87

Reaction equation

CC(C)(C)OC(=O)N1CC=C(B2OC(C)(C)C(C)(C)O2)CC1
4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
O=C([O-])[O-].[K+].[K+]
potassium carbonate
FC(F)(F)c1ccc(Br)cc1
p-bromobenzotrifluoride
→
CC(C)(C)OC(=O)N1CC=C(c2ccc(C(F)(F)F)cc2)CC1
title compound
CC(C)(C)OC(=O)N1CC=C(c2ccc(C(F)(F)F)cc2)CC1
4-(4-Trifluoromethyl-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Reactants

CC(C)(C)OC(=O)N1CC=C(B2OC(C)(C)C(C)(C)O2)CC1
4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
O=C([O-])[O-].[K+].[K+]
potassium carbonate
FC(F)(F)c1ccc(Br)cc1
p-bromobenzotrifluoride

Reagents

None

Solvents

CN(C)C=O
dimethylformamide

Conditions

Temperature
80°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Concentrationconcentrated in vacuo
  2. 2
    Otherpurified by column chromatography (SiO2, 20 g, heptane)

Procedure

To a solution of 0.97 mmol 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (CAS: 286961-14-6) in 6 ml dimethylformamide, 2.91 mmol potassium carbonate, 1.02 mmol p-bromobenzotrifluoride, and 0.06 mmol dichlor(1,1′ bis(diphenylphosphino)ferrocene) palladium(II)dichloromethane complex were successively added. The reaction was then stirred at 80° C. for 6 hours, concentrated in vacuo and purified by column chromatography (SiO2, 20 g, heptane), to give the title compound. MS (m/e): 271.1 (M-isobuthylene)

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07485637B2uspto-grants-2009_02