반응식
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[N:9][CH:10]=[C:4]2[CH:3]=1.C([Li])CCC.[F:23][C:24]([F:38])([F:37])[C:25]([C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([CH3:36])[CH:28]=1)=[O:26]>C1COCC1>[F:38][C:24]([F:23])([F:37])[C:25]([C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[N:9][CH:10]=[C:4]2[CH:3]=1)([C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([CH3:36])[CH:28]=1)[OH:26]참가 물질
반응물 3
생성물 1
시약·촉매·용매 1
실험 절차
To a chilled (−78° C.) solution of 7-bromo-3-(4-fluorophenyl)imidazo[1,5-a]pyridine (58 mg, 0.2 mmol) in anhydrous THF (1 mL) was added n-butyllithium (0.1 mL of a 2.5 M solution in hexanes, 2.5 mmol). After 1 minute, a chilled (−78° C.) solution of 2,2,2-trifluoro-1-(1-methyl-1H-indol-3-yl)ethanone (68 mg, 0.3 mmol) in 1 mL of THF was added. After 5 minutes, the reaction mixture was quenched with 50 mL of brine solution and extracted with three 25 mL portions of methylene chloride. The combined organic extracts were washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford a yellow oil. The residue was purified by column chromatography over silica gel eluting with 0-70% ethyl acetate to afford 30 mg of the title compound as a light yellow solid. MS m/z 440 (MH+).
후처리
- additionwas added
- waitAfter 5 minutes
- customthe reaction mixture was quenched with 50 mL of brine solution
- extractionextracted with three 25 mL portions of methylene chloride
- washThe combined organic extracts were washed with water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customto afford a yellow oil
- customThe residue was purified by column chromatography over silica gel eluting with 0-70% ethyl acetate
출처 및 근거
- ORD 기록
- ord-f76daba1af29439583acd6d6a77d06fb
- 출처 데이터셋
- uspto-grants-2014_02
- 특허 번호
- US08658637B2
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