2-(Bromomethoxy)ethyl acetate → acetic acid 2-(3H-imidazo[4,5-b]pyridin-3-ylmethoxy)-ethyl ester

HRID 2112387

반응식

HRID 2112387 반응식
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][CH:2]=1.CC(C)([O-])C.[K+].[C:16]([O:19][CH2:20][CH2:21][O:22][CH2:23]Br)(=[O:18])[CH3:17]>CN(C=O)C>[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]([CH2:23][O:22][CH2:21][CH2:20][O:19][C:16](=[O:18])[CH3:17])[CH:2]=1

참가 물질

5

반응물 3

HCID 3676562-(Bromomethoxy)ethyl acetateHCID 23665647Potassium tert-butoxideHCID 178420746HCID 178420746, 화합물

생성물 1

HCID 68879998acetic acid 2-(3H-imidazo[4,5-b]pyridin-3-ylmethoxy)-ethyl ester수율 41%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 1.0 g (8.39 mmol) 3H-imidazo[4,5-b]pyridine in 20 ml DMF kept under argon at 0° C. 0.94 g (8.39 mmol) potassium tert-butoxide were added. The solution was warmed to room temperature and after 1 hour a solution of 1.74 g (8.8 mmol) (2-acetoxyethoxy)methyl bromide in 5 ml DMF was added dropwise over half an hour. The reaction was stirred at room temperature for 20 hours and then poured onto 75 ml of ice water. The mixture was extracted twice with 50 ml ethyl acetate. The combined organic layers were washed with water and brine, dried over Na2SO4 filtered and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, gradient DCM, DCM/MeOH 95/5 and 9/1) to afford 0.81 g (41%) of the desired product. MS(ISP): 236.2 [MH]+.

후처리

  1. customkept under argon at 0° C
  2. additionwas added dropwise over half an hour
  3. extractionThe mixture was extracted twice with 50 ml ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography (silica gel, gradient DCM, DCM/MeOH 95/5 and 9/1)

출처 및 근거

ORD 기록
ord-d630aad3c925412699f1721b1e0b125c
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07524823B2

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