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

HRID 605012

反応式

HRID 605012 の反応式
[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

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 178420123HCID 178420123、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-88983181fff04ef885343de7a3355b84
出典データセット
uspto-grants-2011_03
特許番号
US07910561B2

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