반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]2[C:8](=[O:20])[CH2:9][O:10][C:11]3[CH:18]=[CH:17][C:16](Br)=[CH:15][C:12]=3[C:13]=2[N:14]=1)=[O:4].[CH3:21][C:22]([OH:26])([C:24]#[CH:25])[CH3:23].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CCN(CC)CC.CC([O-])=O.CC([O-])=O.[Pd+2].[Cu]I>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]2[C:8](=[O:20])[CH2:9][O:10][C:11]3[CH:18]=[CH:17][C:16]([C:25]#[C:24][C:22]([OH:26])([CH3:23])[CH3:21])=[CH:15][C:12]=3[C:13]=2[N:14]=1)=[O:4]참가 물질
7
반응물 3
생성물 1
시약·촉매·용매 3
반응 조건
- 온도
- 80 °C
실험 절차
A mixture of 9-Bromo-4-oxo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester (200 mg, 0.565 mmol), 2-methyl-3-butyn-2-ol (237 mg, 2.825 mmol), Pd(OAc)2 (13 mg, 0.0565 mmol), CuI (21 mg, 0.113 mmol) and PPh3 (45 mg, 0.17 mmol) in Et3N (10 mL) was degassed with N2, and the mixture was stirred at 80° C. overnight. The reaction was cooled to room temperature, concentrated and purified by flash column chromatography (silica gel, EtOAc in hexane from 0 to 30%) to give 9-(3-Hydroxy-3-methyl-but-1-ynyl)-4-oxo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester as an off-white solid (81 mg, 40%). LC-MS (ESI & APCI): 358.2 (M+1).
후처리
- customwas degassed with N2
- temperatureThe reaction was cooled to room temperature
- concentrationconcentrated
- custompurified by flash column chromatography (silica gel, EtOAc in hexane from 0 to 30%)
출처 및 근거
- ORD 기록
- ord-af41cc050d324ef6a3c77fc43b5e3380
- 출처 데이터셋
- uspto-grants-2015_05
- 특허 번호
- US09034866B2
연결된 노트
불러오는 중…