Toluene → 1-(1,1-dimethylethyl) 3-methyl 4-{4-[(trifluoromethyl)oxy]phenyl}-5,6-dihydro-1,3(2H)-pyridinedicarboxylate

HRID 639850Notes

Reaction equation

HRID 639850 reaction equation
FC(F)(F)S(O[C:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][C:8]=1[C:20]([O:22][CH3:23])=[O:21])(=O)=O.[F:26][C:27]([F:39])([F:38])[O:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[F:26][C:27]([F:38])([F:39])[O:28][C:29]1[CH:34]=[CH:33][C:32]([C:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:9][C:8]=2[C:20]([O:22][CH3:23])=[O:21])=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 152219361-Tert-butyl 3-methyl 4-(trifluoromethanesulfonyloxy)-1,2,5,6-tetrahydropyridine-1,3-dicarboxylate

Product 1

HCID 468560471-(1,1-dimethylethyl) 3-methyl 4-{4-[(trifluoromethyl)oxy]phenyl}-5,6-dihydro-1,3(2H)-pyridinedicarboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 1-(1,1-dimethylethyl) 3-methyl 4-{[(trifluoromethyl)sulfonyl]oxy}-5,6-dihydro-1,3(2H)-pyridinedicarboxylate (2.5 g, P2), {4-[(trifluoromethyl)oxy]phenyl}boronic acid (1.52 g) and Pd(PPh3)4 (265 mg) under nitrogen, toluene (34 mL), ethanol (25 mL) and Na2CO3 (2M, 19 mL) were added in sequence. The mixture was stirred at 80° C. for 2 hours then the reaction mixture was allowed to reach room temperature. The aqueous phase was extracted with Et2O (2 times), the combined organic phases were dried on anhydrous Na2SO4 and the solvent was evaporated obtaining a crude product that was purified by flash-chromatography (eluting with ethyl acetate/cyclohexane from 1:9 to 3:7) to give the title compound (2.5 g)

Workup

  1. customto reach room temperature
  2. extractionThe aqueous phase was extracted with Et2O (2 times)
  3. dry with materialthe combined organic phases were dried on anhydrous Na2SO4
  4. customthe solvent was evaporated
  5. customobtaining a crude product that
  6. customwas purified by flash-chromatography (eluting with ethyl acetate/cyclohexane from 1:9 to 3:7)

Sources & evidence

ORD record
ord-8b4c6b3ee03e4c36b14d06350cc0a428
Source dataset
uspto-grants-2010_04
Patent number
US07691893B2

Reaction notes

Loading…