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

HRID 873398ノート

反応式

HRID 873398 の反応式
[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]

参加物

5

反応物 3

HCID 6362Isopropyl iodide2 回HCID 24758Sodium hydride2 回HCID 11020003Methyl 7-methoxy-1H-indole-4-carboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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, 6 H), 3.95 (s, 3 H), 4.01 (s, 3 H), 5.46 (dt, J=13.39, 6.69 Hz, 1 H), 6.66 (d, J=8.34 Hz, 1 H), 7.15 (d, J=3.03 Hz, 1 H), 7.34 (d, J=3.28 Hz, 1 H), 7.87 (d, J=8.34 Hz, 1 H). MS(ES) [M+H]+ 248.2.

後処理

  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

出典と根拠

ORDレコード
ord-70f01a023036470ab3d7b11048281d5a
出典データセット
uspto-grants-2015_03
特許番号
US08975291B2

反応ノート

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