Water → N-(3-Fluoro-4-pyridinyl)-N-(3-methyl-1H-indol-1-yl)glycine ethyl ester

HRID 440431노트

반응식

HRID 440431 반응식
[H-].[Na+].[F:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[NH:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH3:20])=[CH:12]1.Cl[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].O>CN(C)C=O>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][N:10]([C:9]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[F:3])[N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH3:20])=[CH:12]1)[CH3:27]

참가 물질

6

반응물 4

HCID 962WaterHCID 7751Ethyl chloroacetateHCID 24758Sodium hydrideHCID 9942843N-(3-Fluoro-4-pyridinyl)-3-methyl-1H-indol-1-amine

생성물 1

HCID 15818612N-(3-Fluoro-4-pyridinyl)-N-(3-methyl-1H-indol-1-yl)glycine ethyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

반응 조건

온도
-20 °C

실험 절차

To a suspension of NaH (60% in oil, 1.48 g) in 10 ml of dimethylformamide (DMF) at ice bath temperature was added dropwise a solution of N-(3-fluoro-4-pyridinyl)-3-methyl-1H-indol-1-amine (8.5 g) in 40 ml of DMF. when addition was complete, the mixture was stirred for 15 minutes at ice bath temperature, and then cooled to -20° C. Ethyl chloroacetate (3.95 ml) was added dropwise in 10 ml of DMF. The mixture was stirred at -20° C. for one hour. The mixture was then poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried (sat. NaCl, anhy. MgSO4). After filtering, the solvent was evaporated to yield an oil (12.2 g) which was eluted with 10% ethyl acetate/DCM on a silica gel column via HPLC. The desired fractions were evaporated to yield 6.9 g of a solid, m.p. 105°-108° C.

후처리

  1. additionwhen addition
  2. stirringThe mixture was stirred at -20° C. for one hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (sat. NaCl
  6. filtrationAfter filtering
  7. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-cfc0b6b532734aa9b257e44ebadd2bab
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05519131

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