Cesium carbonate → HCID 88057427、化合物

HRID 629865ノート

反応式

HRID 629865 の反応式
[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

参加物

7

反応物 3

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

生成物 1

HCID 88057427HCID 88057427、化合物

試薬・触媒・溶媒 3

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9943400b9b4f4aaba82048bd45c9c927
出典データセット
uspto-grants-2016_04
特許番号
US09315518B2

反応ノート

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