Sodium Carbonate → 1-(1,1-dimethylethyl) 3-methyl 4-(3,4-dichlorophenyl)-5,6-dihydro-1,3(2H)-pyridinedicarboxylate

HRID 639841Notes

Reaction equation

HRID 639841 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.[Cl:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][C:32]=1[Cl:33].C([O-])([O-])=O.[Na+].[Na+].[NH4+].[Cl-]>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.C1(C)C=CC=CC=1>[Cl:26][C:27]1[CH:28]=[C:29]([C:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][C:8]=2[C:20]([O:22][CH3:23])=[O:21])[CH:30]=[CH:31][C:32]=1[Cl:33]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 27343303,4-Dichlorobenzeneboronic acidHCID 152219361-Tert-butyl 3-methyl 4-(trifluoromethanesulfonyloxy)-1,2,5,6-tetrahydropyridine-1,3-dicarboxylate

Product 1

HCID 468559241-(1,1-dimethylethyl) 3-methyl 4-(3,4-dichlorophenyl)-5,6-dihydro-1,3(2H)-pyridinedicarboxylateYield 99.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

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 (200 mg, P2), 3,4-dichlorophenylboronic acid (108 mg) and Pd(PPh3)4 (21 mg) under nitrogen, toluene (2.5 mL), ethanol (2 mL) and Na2CO3 (aqueous 2M solution, 2 mL) were added in sequence. The mixture was stirred at 80° C. for 1 hour then the reaction mixture was allowed to reach room temperature. Saturated aqueous NH4Cl solution (15 mL) was poured into the solution and the mixture was transferred in a separator funnel. The mixture was extracted with ethyl acetate (3×20 mL), the combined organic phases were dried on anhydrous Na2SO4 and the solvent evaporated obtaining a crude product that was purified by flash-chromatography (eluting with ethyl acetate/cycloexane 1:3) to give the title compound (198 mg).

Workup

  1. customto reach room temperature
  2. customthe mixture was transferred in a separator funnel
  3. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  4. dry with materialthe combined organic phases were dried on anhydrous Na2SO4
  5. customthe solvent evaporated
  6. customobtaining a crude product that
  7. customwas purified by flash-chromatography (eluting with ethyl acetate/cycloexane 1:3)

Sources & evidence

ORD record
ord-8bce1d5765324954bfad7f7330632446
Source dataset
uspto-grants-2010_04
Patent number
US07691893B2

Reaction notes

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