Methyl iodide → [7-Fluoro-2-(4-nitro-phenyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester

HRID 1593045노트

반응식

HRID 1593045 반응식
[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[F:18])[C:14](=[O:19])[N:13]([C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)[CH:12]=[CH:11]2)([CH3:4])([CH3:3])[CH3:2].[C:30](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C>[C:1]([O:5][C:6](=[O:29])[N:7]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[F:18])[C:14](=[O:19])[N:13]([C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)[CH:12]=[CH:11]2)[CH3:30])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 58998509[7-Fluoro-2-(4-nitro-phenyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl]-carbamic acid tert-butyl ester

생성물 1

HCID 58998426[7-Fluoro-2-(4-nitro-phenyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester수율 93%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of [7-Fluoro-2-(4-nitro-phenyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl]-carbamic acid tert-butyl ester (0.36 g, 0.9 mmol) in dry DMF (9 mL) was added cesium carbonate (1.04 g, 3.19 mmol) followed by neat methyl iodide (0.064 mL, 1.03 mmol). The mixture was stirred at room temperature for 3.5 hr, extracted into ethyl acetate (150 mL), washed with water (2×50 mL) and brine (50 mL), dried over sodium sulfate, filtered, concentrated in vacuo and dried to give 0.34 g (93%) of pure [7-Fluoro-2-(4-nitro-phenyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester. RP-HPLC: 5.89 min; ES-MS (M+H)+=414.0; 1H-NMR (DMSO-d6) δ (ppm): 1.33 (s, 9), 3.20 (s, 3), 6.75 (d, 1), 7.52 (d, 1), 7.80 (d, 2), 7.83 (d, 1), 7.93 (d, 1), 8.35 (d, 2).

후처리

  1. extractionextracted into ethyl acetate (150 mL)
  2. washwashed with water (2×50 mL) and brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customdried

출처 및 근거

ORD 기록
ord-3aac9f4857c24feebde908e64fd35023
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07294635B2

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