Cesium fluoride → 4-(4-Pyrimidin-2-yl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1038035Notes

Reaction equation

HRID 1038035 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:26]1[N:31]=[CH:30][CH:29]=[CH:28][N:27]=1)CCC.[F-].[Cs+]>C(PC(C)(C)C)(C)(C)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([C:26]3[N:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 27632512-(Tributylstannyl)pyrimidineHCID 272817821-N-Boc-4-(4-bromophenyl)piperidine

Product 1

HCID 595113424-(4-Pyrimidin-2-yl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 86614436Di-t-butylphosphine palladiumCatalyst

Conditions

Temperature
90 °C

Procedure

A mixture containing 4-(4-bromo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (100 mg, 0.29 mmol), 2-tributylstannanyl-pyrimidine (130 mg, 0.36 mmol), cesium fluoride (85 mg, 0.56 mmol) and palladium di-tert-butylphosphine was degassed three times with Ar. Dioxane was added and the formed reaction mixture was stirred at 90° C. overnight under Ar. Then the reaction mixture was filter through celite and the solvent was removed under vacuum and crude product was used directly in the next step.

Workup

  1. customwas degassed three times with Ar
  2. additionDioxane was added
  3. customthe formed reaction mixture
  4. filtrationThen the reaction mixture was filter through celite
  5. customthe solvent was removed under vacuum and crude product

Sources & evidence

ORD record
ord-8be9a5c9f5454a4cb8071ff654686717
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

Loading…