Cesium carbonate → HCID 88057427, 화합물

HRID 629865노트

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HRID 629865 반응식
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:5]2=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:19][C:20]1([F:25])[CH2:22][CH:21]1[CH2:23]I>CN1C(=O)CCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:12])[C:9](=[O:11])[N:10]([CH2:23][CH:21]3[CH2:22][C:20]3([F:25])[F:19])[C:5]2=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 552690615-chloro-3-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-oneHCID 670560341,1-Difluoro-2-(iodomethyl)cyclopropane

생성물 1

HCID 88057427HCID 88057427, 화합물

시약·촉매·용매 3

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매HCID 516892Sodium Bicarbonate용매

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온도
100 °C

실험 절차

5-Chloro-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1-3, 516 mg, 2.81 mmol) and cesium carbonate (4.97 g, 15.26 mmol) were added to a round bottom flask and suspended in NMP (4.6 mL) under nitrogen. 1,1-Difluoro-2-(iodomethyl)cyclopropane (481 μL, 5.06 mmol) was added to the suspension and then heated to 100° C. in microwave reactor for 10 min. Following this duration, the reaction was cooled to room temperature and suspended in ethyl acetate and sodium bicarbonate. The suspension was washed with sodium bicarbonate, brine(×5), dried over sodium sulfate, filtered, and concentrated. The mixture was purified using reverse-phase chromatography (5-95% 0.1% TFA in H2O:acetonitrile) to give 5-chloro-1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (6-1) as an off-white solid. MS m/z (M+H): calculated=274.0553; observed=274.0551.

후처리

  1. temperaturethe reaction was cooled to room temperature
  2. washThe suspension was washed with sodium bicarbonate, brine(×5)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe mixture was purified

출처 및 근거

ORD 기록
ord-9943400b9b4f4aaba82048bd45c9c927
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315518B2

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