Water → HCID 58547634, compound

HRID 1850291Notes

Reaction equation

HRID 1850291 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19](Cl)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27339503-Tolylboronic acidHCID 58547013Tert-butyl 4-(3-chloropyrazin-2-yl)piperidine-1-carboxylate

Product 1

HCID 58547634HCID 58547634, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of (88) (142 mg, 0.48 mmol) in dioxane (10 mL) was added phenylboronic acid (78) (87 mg, 0.71 mmol), Na2CO3 (152 mg, 1.4 mmol) and H2O (2 mL). The reaction mixture was degassed with N2 and then PdCl2(dppf) (35 mg, 0.05 mmol) was added. The reaction mixture was stirred at 80° C. for 12 h. The reaction mixture was left to reach RT and filtered through a pad of CELITE® and the filter cake was washed with CH2Cl2 (20 mL×3). The combined filtrates were evaporated in vacuo and the residue was purified by column chromatography ((EtOAc:Petrol ether=1:1) to give 4-(3-Phenyl-pyrazin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (89) (128 mg, 0.38 mmol, 80% yield).

Workup

  1. customThe reaction mixture was degassed with N2
  2. waitThe reaction mixture was left
  3. customto reach RT
  4. filtrationfiltered through a pad of CELITE®
  5. washthe filter cake was washed with CH2Cl2 (20 mL×3)
  6. customThe combined filtrates were evaporated in vacuo
  7. customthe residue was purified by column chromatography ((EtOAc:Petrol ether=1:1)

Sources & evidence

ORD record
ord-6a5db6cbeeb84984b790cd40f8efec7b
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

Loading…