Isopropyl iodide → Methyl 1-(1-methylethyl)-7-(methyloxy)-1H-indole-4-carboxylate

HRID 42447노트

반응식

HRID 42447 반응식
[CH3:1][O:2][C:3]1[C:11]2[NH:10][CH:9]=[CH:8][C:7]=2[C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1.[H-].[Na+].I[CH:19]([CH3:21])[CH3:20]>CN(C=O)C>[CH3:20][CH:19]([N:10]1[C:11]2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[C:6]([C:12]([O:14][CH3:15])=[O:13])[C:7]=2[CH:8]=[CH:9]1)[CH3:21]

참가 물질

5

반응물 3

HCID 6362Isopropyl iodide2회HCID 24758Sodium hydride2회HCID 11020003Methyl 7-methoxy-1H-indole-4-carboxylate

생성물 1

HCID 67468655Methyl 1-(1-methylethyl)-7-(methyloxy)-1H-indole-4-carboxylate수율 94.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a cooled (ice/water bath) solution of methyl 7-(methyloxy)-1H-indole-4-carboxylate (350 mg, 1.706 mmol) in DMF (20 mL) was added sodium hydride (56.0 mg, 2.217 mmol). After 10 minutes added 2-iodopropane (0.188 mL, 1.876 mmol). The reaction was stirred at RT for 1 h, followed by heating at 50° C. for 2 h. The reaction was then cooled in an ice water bath and more sodium hydride (56.0 mg, 2.217 mmol) and 2-iodopropane (0.188 mL, 1.876 mmol) were added. The reaction was heated at 50° C. for 3 h, at which time it was concentrated. The residue was dissolved in DCM and washed with water and brine, dried over MgSO4, filtered and concentrated to give 400 mg of the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.49 (d, 6H), 3.95 (s, 3H), 4.01 (s, 3H), 5.46 (dt, J=13.39, 6.69 Hz, 1H), 6.66 (d, J=8.34 Hz, 1H), 7.15 (d, J=3.03 Hz, 1H), 7.34 (d, J=3.28 Hz, 1H), 7.87 (d, J=8.34 Hz, 1H). MS (ES) [M+H]+ 248.2.

후처리

  1. temperatureby heating at 50° C. for 2 h
  2. temperatureThe reaction was then cooled in an ice water bath
  3. temperatureThe reaction was heated at 50° C. for 3 h, at which time it
  4. concentrationwas concentrated
  5. dissolutionThe residue was dissolved in DCM
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-080dd5acd25040359a48dfeb0ac2c5d2
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536179B2

반응 노트

불러오는 중…