Potassium Carbonate → [4'-(5-Methyl-[1,3,4]oxadiazol-2-yl)-biphenyl-4-yl]-(2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

HRID 1677130Notes

Reaction equation

HRID 1677130 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:13])=[N:11][N:12]=2)=[CH:4][CH:3]=1.[N:14]1([CH2:19][C@@H:20]2[CH2:24][CH2:23][CH2:22][N:21]2[C:25]([C:27]2[CH:32]=[CH:31][C:30](B3OC(C)(C)C(C)(C)O3)=[CH:29][CH:28]=2)=[O:26])[CH2:18][CH2:17][CH2:16][CH2:15]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)C>[CH3:13][C:10]1[O:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:30]3[CH:31]=[CH:32][C:27]([C:25]([N:21]4[CH2:22][CH2:23][CH2:24][CH:20]4[CH2:19][N:14]4[CH2:15][CH2:16][CH2:17][CH2:18]4)=[O:26])=[CH:28][CH:29]=3)=[CH:3][CH:4]=2)=[N:12][N:11]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 75806TricyclohexylphosphineHCID 28294152-(4-chlorophenyl)-5-methyl-1,3,4-oxadiazoleHCID 57980137HCID 57980137, compound

Product 1

HCID 11582434[4'-(5-Methyl-[1,3,4]oxadiazol-2-yl)-biphenyl-4-yl]-(2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolvent

Procedure

Procedure D′: To a microwave reactor vessel, add 2-(4-Chloro-phenyl)-5-methyl-[1,3,4]oxadiazole (1.0 mmol; CAS (22815-98-1), (2-(S)-Pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone (See Intermediate Preparation 23) (2.5 mmol), palladium (II) acetate (0.025 mmol), tricyclohexylphosphine (0.05 mmol), potassium carbonate (5.0 mmol) and ethanol (0.10M). Run the reaction in a CEM microwave reactor for four hours at 90° C. with 80 W power and cooling. After this time, wash the reaction with 1N hydrochloric acid while extracting with dichloromethane. Dry the organics with sodium sulfate, decant and concentrate in vacuo. Purify the title compound via radial chromatography eluting with 2M ammonia in methanol and dichloromethane. MS (m/e): 417.3 (M+1)

Workup

  1. customthe reaction in a CEM microwave reactor for four hours at 90° C. with 80 W power
  2. temperaturecooling
  3. washAfter this time, wash
  4. customthe reaction with 1N hydrochloric acid
  5. extractionwhile extracting with dichloromethane
  6. dry with materialDry the organics with sodium sulfate
  7. customdecant
  8. concentrationconcentrate in vacuo
  9. customPurify the title compound via radial chromatography
  10. washeluting with 2M ammonia in methanol and dichloromethane

Sources & evidence

ORD record
ord-081a9ac4abfa461abc9b21d5098f4e30
Source dataset
uspto-grants-2011_08
Patent number
US08008301B2

Reaction notes

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