Chloromethyl ethyl ether → 1-ethoxymethyl-5-methoxy-3-(1-methylethoxy)-1H-indole-2-carboxamide

HRID 21600

反応式

HRID 21600 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH2:14])=[O:13])=[C:6]2[O:15][CH:16]([CH3:18])[CH3:17].[H-].[Na+].[CH2:21]([O:23][CH2:24]Cl)[CH3:22]>CN(C)C=O.CCCCCC>[CH2:21]([O:23][CH2:24][N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[C:6]([O:15][CH:16]([CH3:18])[CH3:17])=[C:7]1[C:12]([NH2:14])=[O:13])[CH3:22]

参加物

6

反応物 3

HCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 107530635-Methoxy-3-(1-methylethoxy)-1H-indole-2-carboxamide

生成物 1

HCID 152945341-ethoxymethyl-5-methoxy-3-(1-methylethoxy)-1H-indole-2-carboxamide収率 59.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

5-Methoxy-3-(1-methylethoxy)-1H-indole-2-carboxamide (328 mg, 1.32 mmol) in 5 mL of dimethylformamide is added to a suspension of sodium hydride (60% by weight) (67 mg, 1.67 mol) in 5 mL of dimethylformamide. After 1.5 hours the mixture is cooled to 0° C. and chloromethyl ethyl ether (160 μL, 1.72 mmol) is added dropwise, and the solution is stirred at 0° C. for 20 minutes and then at room temperature for 1.5 hours. The reaction mixture is diluted with 1:1 hexane:ethyl acetate and washed with brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo. Chromatography eluting with 1:1 ethyl acetate:hexane gives 240 mg (51%) of 1-ethoxymethyl-5-methoxy-3-(1-methylethoxy)-1H-indole-2-carboxamide; mp 110°-112° C.

後処理

  1. waitat room temperature for 1.5 hours
  2. washethyl acetate and washed with brine
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washChromatography eluting with 1:1 ethyl acetate

出典と根拠

ORDレコード
ord-859a8129a115414292c81e086605f598
出典データセット
uspto-grants-1995_06
特許番号
US05424329

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