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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
ノート
印刷プレビュー

反応式

HRID 1867786 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845
palladium(II) acetate
触媒
HCID 702Ethanol溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-b8fa8334ac9641059dcabcc629fdfcd0
出典データセット
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07632857B2

反応ノート

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