Potassium Carbonate → tert-butyl 4-(4-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 1723641Notes

Reaction equation

HRID 1723641 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11](B2OC(C)(C)C(C)(C)O2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[C:30]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=1>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 18364827tert-butyl 4-(4-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

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)

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by column chromatography (SiO2, 20 g, heptane)

Sources & evidence

ORD record
ord-e59ba8f944534bc182c9ff8f6ed4ff87
Source dataset
uspto-grants-2009_02
Patent number
US07485637B2

Reaction notes

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