Sodium Carbonate → HCID 46855918, compound

HRID 639854Notes

Reaction equation

HRID 639854 reaction equation
FC(F)(F)S(O[C:7]1[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH:12]=1)(=O)=O.[Cl:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][C:28]=1[Cl:29].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:22][C:23]1[CH:24]=[C:25]([C:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH:12]=2)[CH:26]=[CH:27][C:28]=1[Cl:29]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 27343303,4-Dichlorobenzeneboronic acidHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 46855918HCID 46855918, compoundYield 80.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 1,1-dimethylethyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydro-1(2H)-pyridinecarboxylate (P52, 500 mg), 3,4-dichlorophenylboronic acid (330 mg) and Pd(PPh3)4 (50 mg) under nitrogen, toluene (6.5 mL), ethanol (5 mL) and Na2CO3 (2M, 5 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. Saturated NH4Cl (30 mL) was poured into the solution and the mixture was transferred in a separator funnel. The mixture was extracted with ethyl acetate (3×40 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 1:9) to give the title compound (400 mg).

Workup

  1. customto reach room temperature
  2. customthe mixture was transferred in a separator funnel
  3. extractionThe mixture was extracted with ethyl acetate (3×40 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 1:9)

Sources & evidence

ORD record
ord-873e44bc76644d22a00673b8bca87352
Source dataset
uspto-grants-2010_04
Patent number
US07691893B2

Reaction notes

Loading…