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

HRID 21600

반응식

HRID 21600 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8058Hexane용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-859a8129a115414292c81e086605f598
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424329

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