Cesium fluoride → HCID 68577637, compound

HRID 2415167Notes

Reaction equation

HRID 2415167 reaction equation
Br[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.[C:21]1(OB(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[F-].[Cs+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:21]1([C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)[CH:5]=[CH:4][CH:3]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 25953Cesium fluorideHCID 78412Phenyl dihydrogen orthoborateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 160590464-Boc-1-(6-bromo-2-pyridyl)piperazine

Product 1

HCID 68577637HCID 68577637, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2 g (5.84 mmol) of tert.butyl 4-(6-bromo-pyridin-2-yl)-piperazine-1-carboxylate, 0.75 g (6.15 mmol) of phenylboric acid, 2.66 g (17.52 mmol) of caesium fluoride, 0.045 g (0.15 mmol) of 2-(di-t-butylphosphino)-biphenyl and 0.013 g (0.06 mmol) of palladium acetate in 20 ml of dioxane is stirred for six hours at 50° C. under nitrogen. Then it is diluted with water and the reaction mixture is extracted with ethyl acetate. The organic phase is separated off and dried over sodium sulphate. Purification is by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate=4:1).

Workup

  1. extractionthe reaction mixture is extracted with ethyl acetate
  2. customThe organic phase is separated off
  3. dry with materialdried over sodium sulphate
  4. customPurification

Sources & evidence

ORD record
ord-3b84e28124a0406f8caf8f62a0e66e56
Source dataset
uspto-grants-2004_11
Patent number
US06818644B1

Reaction notes

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