Triethyl phosphonoacetate → Ethyl 2-(2-(Benzyloxy)-7,8-dihydropyrido[1,2-a]indol-9(6H)-ylidene)acetate

HRID 1964159ノート

反応式

HRID 1964159 の反応式
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH2:17]([O:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]1[CH2:34][CH2:35][CH2:36][C:37](=O)[C:29]1=[CH:28]2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[NH4+].[Cl-]>CN(C=O)C>[CH2:17]([O:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]1[CH2:34][CH2:35][CH2:36][C:37](=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:29]1=[CH:28]2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 672501482-(Benzyloxy)-7,8-dihydropyrido[1,2-a]indol-9(6H)-one

生成物 1

HCID 67249894Ethyl 2-(2-(Benzyloxy)-7,8-dihydropyrido[1,2-a]indol-9(6H)-ylidene)acetate収率 86%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of ethyl 2-(diethoxyphosphoryl)acetate (3.11 mL, 15.65 mmol) in DMF (10 mL) was added sodium hydride (60% dispersion in mineral oil) (626 mg, 15.65 mmol) at 0° C. The reaction was slowly warmed to room temperature and stirred for 10 min. 2-(Benzyloxy)-7,8-dihydropyrido[1,2-a]indol-9(6H)-one (570 mg, 1.956 mmol) in DMF was added. The reaction was heated at 65° C. for 2 h, cooled down, poured into saturated NH4Cl aqueous solution, and extracted with ethyl acetate. The combined organics were washed with water, dried over anhydrous Na2SO4, and concentrated. The residue was purified by silica gel column chromatography to give the title compound (608 mg). LCMS m/z=362.5 [M+H]+.

後処理

  1. temperatureThe reaction was heated at 65° C. for 2 h
  2. temperaturecooled down
  3. extractionextracted with ethyl acetate
  4. washThe combined organics were washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-fb655a4544ea469b8760183ec0805aaf
出典データセット
uspto-grants-2013_04
特許番号
US08415484B2

反応ノート

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