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Tetrahydrofuran → 5-(4-(2,5-bis(4-nitrophenyl)pyrrolidin-1-yl)phenyl)-N,N-dimethylpyridin-2-amine

HRID 2364825
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HRID 2364825 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)[CH2:11][CH2:10][CH:9]2[C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.[CH3:31][N:32]([CH3:42])[C:33]1[N:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1COCC1>[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2].O>[N+:19]([C:16]1[CH:15]=[CH:14][C:13]([CH:12]2[CH2:11][CH2:10][CH:9]([C:22]3[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=3)[N:8]2[C:5]2[CH:6]=[CH:7][C:2]([C:36]3[CH:35]=[CH:34][C:33]([N:32]([CH3:42])[CH3:31])=[N:38][CH:37]=3)=[CH:3][CH:4]=2)=[CH:18][CH:17]=1)([O-:21])=[O:20]
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참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 62657Potassium Phosphate, TribasicHCID 27632716-(Dimethylamino)pyridine-3-boronic acidHCID 866491071-(4-Bromophenyl)-2,5-bis(4-nitrophenyl)pyrrolidine

생성물 1

HCID 866491085-(4-(2,5-bis(4-nitrophenyl)pyrrolidin-1-yl)phenyl)-N,N-dimethylpyridin-2-amine수율 96%

시약·촉매·용매 2

HCID 178454861HCID 178454861, 화합물촉매HCID 962Water용매

실험 절차

The product from Example 86A (25.7 mg, 0.055 mmole) was combined in a microwave tube with 6-(dimethylamino)pyridine-3-ylboronic acid (17.49 mg, 0.105 mmole), tribasic potassium phosphate (24.70 mg, 0.116 mole) and 1,1′-bis(di-tert-butylphosphino)ferrocene palladium dichloride (2.504 mg, 3.84 μmole). The tube was sealed and a solvent mixture of THF (2 mL) and water (0.6 mL) added via syringe. The reaction mixture was sparged with nitrogen at room temperature for three minutes during which time the solution turned black in color. Chromatographic analysis indicated that the reaction was complete. The contents of the microwave tube were partitioned between brine (3 mL) and ethyl acetate (3 mL). The water was drawn off and the organic phase dried over MgSO4, filtered and concentrated. The crude product was purified by chromatography on silica gel from 2 up to 20% ethyl acetate in hexane to provide the title compound (26.8 mg, 96% yield) as an orange solid as a mixture of stereoisomers. MS ESI(+) m/z @ 510.4 (M+H)+.

후처리

  1. customThe tube was sealed
  2. additionadded via syringe
  3. customThe reaction mixture was sparged with nitrogen at room temperature for three minutes during which time the solution
  4. customThe contents of the microwave tube were partitioned between brine (3 mL) and ethyl acetate (3 mL)
  5. dry with materialthe organic phase dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography on silica gel from 2 up to 20% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-dc215b351b9f41e88b7015a7e1277f6d
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08691938B2

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