Cesium carbonate → HCID 90412745, 화합물

HRID 1522048노트

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HRID 1522048 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[NH:15][C:16]([CH:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]4)=[CH:17][C:10]=23)O1.Br[C:33]1[N:38]=[C:37]([NH2:39])[CH:36]=[N:35][CH:34]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[NH2:39][C:37]1[N:38]=[C:33]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[NH:15][C:16]([CH:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]4)=[CH:17][C:10]=23)[CH:34]=[N:35][CH:36]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 75806TricyclohexylphosphineHCID 126931822-Amino-6-bromopyrazineHCID 90413258HCID 90413258, 화합물

생성물 1

HCID 90412745HCID 90412745, 화합물

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A mixture of Example 21A (500 mg, 1.2 mmol), 6-bromopyrazin-2-amine (244 mg, 1.4 mmol), bis(triphenylphosphine)palladium(ii) chloride (82 mg, 0.1 mmol), tricyclohexylphosphine (33 mg, 0.1 mmol) and cesium carbonate (1.2 g, 3.5 mmol) was purged with nitrogen, then anhydrous dioxane (60 ml) was added. The mixture was heated at 100° C. overnight. The reaction was cooled to room temperature and filtrated, and the solid was washed with dichloromethane (200 mL). The filtrate was concentrated and purified by flash chromatography on silica gel using an ISCO Companion eluting with heptanes/ethyl acetate (30%) to provide the title compound. MS (ESI+) m/z 395 (M+H)+.

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltrated
  3. washthe solid was washed with dichloromethane (200 mL)
  4. concentrationThe filtrate was concentrated
  5. custompurified by flash chromatography on silica gel using an ISCO Companion
  6. washeluting with heptanes/ethyl acetate (30%)

출처 및 근거

ORD 기록
ord-c816803ab5c44db384979131113b5bcd
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073922B2

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