Methyl iodide → HCID 58554132, 화합물

HRID 2410500노트

반응식

HRID 2410500 반응식
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[CH3:17])=[C:8]([CH2:10][OH:11])[CH:9]=1.[CH3:18]I>CN(C=O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[CH3:17])=[C:8]([CH2:10][O:11][CH3:18])[CH:9]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58554152HCID 58554152, 화합물

생성물 1

HCID 58554132HCID 58554132, 화합물수율 98.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of sodium hydride (2.84 g, 119 mmol) in anhydrous DMF (80 mL) was added a solution of [5-Bromo-2-(2-methylpyrrolidin-1-yl)phenyl]methanol (16 g, 59.2 mmol) in DMF (50 mL) drop wise at 0° C. After 30 minutes, methyl iodide (7.3 mL, 119 mmol) was added drop wise at 0° C. The reaction mixture was quenched with a saturated aqueous solution of NH4Cl (20 mL), then diluted with water (200 mL) and extracted with EtOAc (150 ml). The organic layer was dried (Na2SO4) and concentrated under reduced pressure to afford the title compound as a yellow oil (16.5 g, 98%). 1H NMR (CDCl3, 400 MHz) δ 7.55 (1H, s), 7.29 (1H, m), 6.86 (1H, d), 4.45 (2H, s), 3.55 (1H, m), 3.41 (1H, m), 2.82 (1H, m), 2.12-2.51 (1H, m), 1.91 (1H, m) 1.81 (1H, m), 1.58 (1H, m), 0.99 (3H, d).

후처리

  1. customThe reaction mixture was quenched with a saturated aqueous solution of NH4Cl (20 mL)
  2. additiondiluted with water (200 mL)
  3. extractionextracted with EtOAc (150 ml)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-472f338ea3a3409b948502d37098e1d2
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815919B2

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