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Ethyl Acetate → Tert-butyl 4-(5-acetyl-3-chloropyridin-2-yl)piperazine-1-carboxylate

HRID 912877
Notes
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Reaction equation

HRID 912877 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21](=[O:26])N(OC)C)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Mg+].[Br-].[C:30]([O-])(O)=O.[Na+].CCOC(C)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21](=[O:26])[CH3:30])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 11646699Tert-butyl 4-(3-chloro-5-(methoxy(methyl)carbamoyl)pyridin-2-yl)piperazine-1-carboxylateHCID 178418689HCID 178418689, compound

Product 1

HCID 11631471Tert-butyl 4-(5-acetyl-3-chloropyridin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-[3-chloro-5-(methoxy-methyl-carbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester from step (b) above (1.0 g, 2.6 mmol) in anhydrous THF (20 mL) was added MeMgBr (2.6 mL, 3M solution in Et2O, 7.8 mmol, Aldrich) with stirring at 0° C. The reaction mixture was stirred at room temperature for 4 h and poured into satd. aq. NaHCO3 solution (20 mL). After the addition of EtOAc (50 mL), the mixture was washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (70% EtOAc in hexane) to give the title compound as a white solid. MS (ESI, pos. ion) m/z: 340 (M+1).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 4 h
  2. additionpoured into satd
  3. washthe mixture was washed with brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (70% EtOAc in hexane)

Sources & evidence

ORD record
ord-35677e5e72684381ae6a39a6370c2bb1
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08026241B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes