반응식
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=[CH:4][C:3]=1[F:10].CN(CCN(CCN(C)C)C)C.[Li]CCCC.[Br:28][C:29]1[N:30]=[C:31]([CH:53]=[O:54])[N:32]([C:34]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:33]=1>C1COCC1>[Br:28][C:29]1[N:30]=[C:31]([CH:53]([C:4]2[CH:5]=[C:6]([CH2:8][CH3:9])[CH:7]=[C:2]([Cl:1])[C:3]=2[F:10])[OH:54])[N:32]([C:34]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:33]=1참가 물질
반응물 4
생성물 1
시약·촉매·용매 1
반응 조건
- 온도
- -40 °C
실험 절차
To a solution of Intermediate 221.1 (100 mg, 0.631 mmol) and PMDTA (0.15 mL) in 5 mL THF at −70° C., was added BuLi (1.4 M in hexanes, 0.473 mL, 0.662 mmol). The mixture was stirred with warming to −40° C. over 30 min, recooled to −70° C., then a solution of Intermediate 175.1 (263 mg, 0.631 mmol) in 2 mL THF was added. The mixture was slowly warmed to −20° C. over 1 h. The reaction was quenched with sat. NH4Cl, then was diluted with EtOAc. The organic phase was washed with H2O (2×) and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 40% EtOAc/hexanes gradient) to afford 312 g of Intermediate 221.2 as a colorless solid. LCMS (50 to 100% B, 4 min gradient, A=95% H2O/5% CH3CN/0.1% TFA, B=5% H2O/95% CH3CN/0.1% TFA) RT=5.45 min, 575.28 (M+H)+.
후처리
- customrecooled to −70° C.
- temperatureThe mixture was slowly warmed to −20° C. over 1 h
- customThe reaction was quenched with sat. NH4Cl
- additionwas diluted with EtOAc
- washThe organic phase was washed with H2O (2×) and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe crude product was purified by flash chromatography (0 to 40% EtOAc/hexanes gradient)
출처 및 근거
- ORD 기록
- ord-3cfa38135adf4a4b9a61ce3eb6ddf110
- 출처 데이터셋
- uspto-grants-2009_08
- 특허 번호
- US07576098B2
연결된 노트
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