Cesium carbonate → HCID 53380742, 화합물

HRID 1771549

반응식

HRID 1771549 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:3]=1.[CH:14]1([NH:17][C:18](=[O:35])[NH:19][C:20]2[CH:25]=[CH:24][C:23](B3OC(C)(C)C(C)(C)O3)=[CH:22][CH:21]=2)[CH2:16][CH2:15]1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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>[CH:14]1([NH:17][C:18]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:2]3[CH:7]=[CH:6][N:5]=[C:4]([N:8]4[CH2:13][CH2:12][O:11][CH2:10][CH2:9]4)[N:3]=3)=[CH:22][CH:21]=2)=[O:35])[CH2:16][CH2:15]1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 8246434-(4-Chloropyrimidin-2-yl)morpholineHCID 44119149N-Cyclopropyl-N'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

생성물 1

HCID 53380742HCID 53380742, 화합물수율 6%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 4-(4-chloropyrimidin-2-yl)morpholine (80 mg, 0.40 mmol) and (4-(3-cyclopropylureido)phenyl)boronic acid pinacol ester (145 mg, 0.48 mmol) in dioxane (2 mL) was added Pd(PPh3)2Cl2 (14 mg, 0.02 mmol) and Cs2CO3 (2M aq solution, 0.3 mL). The reaction mixture was then heated to reflux for 16 h. The crude reaction mixture was then partitioned between water and EtOAc, the phases separated and the organic layer washed with aqueous NaHCO3 and brine, dried over magnesium sulfate, filtered and the solvent removed in vacuo. The residue was purified by flash chromatography (0-5% EtOAc/MeOH) to yield a white solid (7.8 mg, 6%).

후처리

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 16 h
  3. customThe crude reaction mixture
  4. customwas then partitioned between water and EtOAc
  5. customthe phases separated
  6. washthe organic layer washed with aqueous NaHCO3 and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed in vacuo
  10. customThe residue was purified by flash chromatography (0-5% EtOAc/MeOH)

출처 및 근거

ORD 기록
ord-696307e215554ca484a981da7f3b5f94
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249129B2

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