반응식
Br[C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[NH:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[O:46]1[CH2:47][CH2:48][N:43]([C:2]2[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=2)[CH2:44][CH2:45]1참가 물질
반응물 4
생성물 1
시약·촉매·용매 3
반응 조건
- 온도
- 65 °C
실험 절차
To a stirred solution of 5-bromopyridin-3-amine (1.5 g, 8.67 mmol), X-Phos (0.33 g, 0.69 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.32 g, 0.35 mmol) and morpholine (3.78 g, 43.3 mmol) in THF (17.3 mL) was added a 1.0M solution of lithium bis(trimethylsilyl)amide in THF (47.7 mL, 47.7 mmol). The resulting mixture was heated to 65° C. and stirring continued for 3 h. After which, the reaction was cooled to rt and then poured into water (100 mL) and extracted with EtOAc (2×150 mL) and DCM (2×150 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (0 to 100% DCM in EtOAc) to give 5-morpholinopyridin-3-amine. Mass Spectrum (ESI) m/e=180.1 (M+1).
후처리
- temperatureAfter which, the reaction was cooled to rt
- extractionextracted with EtOAc (2×150 mL) and DCM (2×150 mL)
- dry with materialThe combined organic layers were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product was purified by column chromatography on silica gel (0 to 100% DCM in EtOAc)
출처 및 근거
- ORD 기록
- ord-6999f84ab3ab44a2892c858e2cf45bf7
- 출처 데이터셋
- uspto-grants-2015_01
- 특허 번호
- US08940724B2
연결된 노트
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