Potassium Carbonate → N-((2'-fluoro-[2,4'-bipyridin]-5-yl)methyl)-2-oxo-2H-[1,3'-bipyridine]-6'-carboxamide
반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([F:24])[CH:19]=3)=[N:16][CH:17]=2)=[O:9])=[N:6][CH:7]=1.[OH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.CN[C@@H]1CCCC[C@H]1NC.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[F:24][C:20]1[CH:19]=[C:18]([C:15]2[CH:14]=[CH:13][C:12]([CH2:11][NH:10][C:8]([C:5]3[N:6]=[CH:7][C:2]([N:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]4=[O:25])=[CH:3][CH:4]=3)=[O:9])=[CH:17][N:16]=2)[CH:23]=[CH:22][N:21]=1참가 물질
7
반응물 4
생성물 1
시약·촉매·용매 2
반응 조건
- 온도
- 108 °C
실험 절차
A mixture of 5-bromo-N-42′-fluoro-[2,4′-bipyridin]-5-yl)methyl)picolinamide 38-4 (38.6 mg, 0.1 mmol), 2-hydroxypyridine 44-1 (19.0 mg, 0.2 mmol), CuI (9.5 mg, 0.05 mmol), trans-N1,N2-dimethylcyclohexane-1,2-diamine (7.1 mg, 0.05 mmol) and K2CO3 (28 mg, 0.20 mmol) in toluene (0.6 mL) was stirred at 108° C. for 8 hours. After cooling to room temperature, the mixture was filtered through celite (washed with ethyl acetate) and the filtrate was concentrated with rotavap. The residue was subjected to preparative reverse phase HPLC separation to give N-42′-fluoro-[2,4′-bipyridin]-5-yl)methyl)-2-oxo-2H-[1,3′-bipyridine]-6′-carboxamide 44 as a solid.
후처리
- temperatureAfter cooling to room temperature
- filtrationthe mixture was filtered through celite (washed with ethyl acetate)
- concentrationthe filtrate was concentrated with rotavap
- customThe residue was subjected to preparative reverse phase HPLC separation
출처 및 근거
- ORD 기록
- ord-4175095b8e60402083459e4fcc7226c9
- 출처 데이터셋
- uspto-grants-2015_11
- 특허 번호
- US09181235B2
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