Water → (6-Phenyl-4-pyrrolidin-1-yl-pyridin-2-yl)-(4-trifluoromethoxy-phenyl)-amine

HRID 1437752Notes

Reaction equation

HRID 1437752 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[CH:5]=[C:4]([N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:3]=1.CC(C)([O-])C.[K+].[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:31]1([C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=3)[CH:5]=[C:4]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:3]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 962WaterHCID 66827Phenylboronic AcidHCID 11667597(6-Chloro-4-pyrrolidin-1-yl-pyridin-2-yl)-(4-trifluoromethoxy-phenyl)-amineHCID 23665647Potassium tert-butoxide

Product 1

HCID 11560366(6-Phenyl-4-pyrrolidin-1-yl-pyridin-2-yl)-(4-trifluoromethoxy-phenyl)-amineYield 55.9%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (6-chloro-4-pyrrolidin-1-yl-pyridin-2-yl)-(4-trifluoromethoxy-phenyl)-amine (120 mg, 0.336 mmol) in 1,4-dioxane (8 mL) was added potassium-tert-butoxide (75 mg, 0.670 mmol) and tetrakis(triphenylphosphine)palladium (0) (20 mg, 0.017 mmol), followed by phenyl boronic acid (102 mg, 0.836 mmol). The resulting reaction mixture was refluxed for 10 hours, after which time water was added 100 mL to the reaction mixture, and the product was extracted with ethyl acetate (100 mL×3). The organic layer was dried over sodium sulphate, filtered, and the filtrate was concentrated under vacuum. The resulting product was purified by column chromatography using 230-400 mesh silica gel (20:80 acetone:petroleum ether) to afford the desired compound (75 mg, purity 99%, yield 6%.).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 10 hours
  3. extractionthe product was extracted with ethyl acetate (100 mL×3)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under vacuum
  7. customThe resulting product was purified by column chromatography

Sources & evidence

ORD record
ord-960cf68d6d924ecb9190200b7ce33284
Source dataset
uspto-grants-2009_11
Patent number
US07622486B2

Reaction notes

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