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

HRID 2364825
Notes
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Reaction equation

HRID 2364825 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178454861HCID 178454861, compoundCatalystHCID 962WaterSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-dc215b351b9f41e88b7015a7e1277f6d
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08691938B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes