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

HRID 1867786
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HRID 1867786 반응식
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
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참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845
palladium(II) acetate
촉매
HCID 702Ethanol용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-b8fa8334ac9641059dcabcc629fdfcd0
출처 데이터셋
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07632857B2

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