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Sodium hydride → tert-butyl 4-(4-pyridin-2-yl-1H-imidazol-1-yl)piperidine-1-carboxylate

HRID 605012
Notes
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Reaction equation

HRID 605012 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)[N:3]=[CH:2]1.[H-].[Na+].CS(O[CH:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1)(=O)=O>CN(C=O)C.C(Cl)Cl>[N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:4]1[N:3]=[CH:2][N:1]([CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 178420123HCID 178420123, compound

Product 1

HCID 67055580tert-butyl 4-(4-pyridin-2-yl-1H-imidazol-1-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 2-(1H-imidazol-4-yl)pyridine (0.87 g, 6 mmol) in DMF (12 mL) at 0° C. was added sodium hydride (346 mg, 7.2 mmol). The reaction mixture was allowed to warm to room temperature and stirred for an additional 20 min. tert-Butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate (1.34 g, 4.8 mmol) was added and the resulting mixture was heated at 80° C. for 48 h. The reaction was cooled to room temperature, diluted with CH2Cl2, and washed with water and brine. The combined organic layers were dried over magnesium sulfate and the solvents removed in vacuo. The residue was purified by silica gel chromatography (0%-100% MeOH/CH2Cl2) and then by HPLC (phenomenex column, 30%-100% acetonitrile/water+0.1% TFA) to afford tert-butyl 4-(4-pyridin-2-yl-1H-imidazol-1-yl)piperidine-1-carboxylate as an oil. 1H NMR (500 MHz, CD3OD) δ 8.88 (m, 1H), 8.70 (m, 1H), 8.40 (m, 1H), 8.10 (m, 1H), 8.00 (m, 1H), 7.55 (m, 1H), 4.58 (m, 1H), 4.32 (m, 2H), 3.01 (m, 2H), 2.24 (m, 2H), 2.00 (m, 2H), 1.49 (s, 9H).

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was heated at 80° C. for 48 h
  3. temperatureThe reaction was cooled to room temperature
  4. washwashed with water and brine
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. customthe solvents removed in vacuo
  7. customThe residue was purified by silica gel chromatography (0%-100% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-88983181fff04ef885343de7a3355b84
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07910561B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes