Water → HCID 11639635, compound

HRID 1437758Notes

Reaction equation

HRID 1437758 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)[CH:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.CC(C)([O-])C.[K+].[NH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34](=[O:36])[CH3:35])=[CH:30][CH:29]=1.O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[OH:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6]2[CH:5]=[C:4]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:3]=[C:2]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([C:34](=[O:36])[CH3:35])=[CH:30][CH:29]=3)[CH:7]=2)[CH2:9][CH2:10]1

Participants

8

Reactant 4

HCID 962WaterHCID 7468p-AminoacetophenoneHCID 11601706HCID 11601706, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 11639635HCID 11639635, compoundYield 57.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Procedure

To a solution of 2′-chloro-6′-phenyl-3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-4-ol (40 mg, 0.13 mmol) in toluene (4 mL) were added potassium tert-butoxide (31 mg, 0.26 mmol), palladium(II)acetate (3 mg, 0.156 mmol), BINAP (4 mg, 0.0065 mmol) and 1-(4-aminophenyl)-ethanone (22 mg, 0.156 mmol) in a 10 mL reaction vessel. This reaction mixture was subjected the microwave radiation, in which the microwave power was 250 W, to attain a reaction temperature of 150° C. After this reaction proceeded for 30 min, water (5 mL) was added to the reaction mixture and the reaction product was extracted with ethyl acetate. The organic layer was dried over sodium sulphate, filtered, and the filtrate concentrated under vacuum. The product was purified through column chromatography using 230-400 mesh silica gel (5% methanol in dichloromethane) to afford the desired compound as a yellow solid (29 mg, yield 55%, purity 96%).

Workup

  1. customin a 10 mL reaction vessel
  2. customa reaction temperature of 150° C
  3. extractionthe reaction product was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe product was purified through column chromatography

Sources & evidence

ORD record
ord-088be91f8e614094b50fdc57d613c927
Source dataset
uspto-grants-2009_11
Patent number
US07622486B2

Reaction notes

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