Cesium carbonate → Ethyl 8-[(3-fluoropyridin-2-yl)methoxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate

HRID 1844186노트

반응식

HRID 1844186 반응식
Cl.Cl[CH2:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][N:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH:17][C:18]1[C:19]2[N:20]([C:25]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:26]([CH3:28])[N:27]=2)[CH:21]=[C:22]([CH3:24])[CH:23]=1>CN(C=O)C>[F:10][C:9]1[C:4]([CH2:3][O:17][C:18]2[C:19]3[N:20]([C:25]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:26]([CH3:28])[N:27]=3)[CH:21]=[C:22]([CH3:24])[CH:23]=2)=[N:5][CH:6]=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 197038622-(Chloromethyl)-3-fluoropyridine HydrochlorideHCID 86717883Ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate

생성물 1

HCID 86718213Ethyl 8-[(3-fluoropyridin-2-yl)methoxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

15.78 g (86.7 mmol) of 2-(chloromethyl)-3-fluoropyridine hydrochloride (commercially available; additionally described in: U.S. Pat. No. 5,593,993 A1, 1997; WO2007/2181 A2, 2007) and 94.06 g (288.9 mmol) of caesium carbonate were added to 16.92 g (72.2 mmol) of ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate from Example 87A in 956 ml of DMF. The reaction mixture was stirred at 60° C. overnight. The reaction mixture was cooled to RT and filtered, the filtercake was washed with ethyl acetate and the filtrate was concentrated. About 500 ml of water were added to the residue and the precipitated solid was filtered off and dried under high vacuum. This gave 24.1 g (93% of theory) of the target compound.

후처리

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered
  3. washthe filtercake was washed with ethyl acetate
  4. concentrationthe filtrate was concentrated
  5. additionAbout 500 ml of water were added to the residue
  6. filtrationthe precipitated solid was filtered off
  7. customdried under high vacuum

출처 및 근거

ORD 기록
ord-36e3aa79bf064e73a81448d376572306
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946215B2

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