Ethanol → 4-(2,4-Dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carbonitrile

HRID 1926630노트

반응식

HRID 1926630 반응식
Cl[C:2]1[N:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[S:5][C:6]=1[C:7]#[N:8].[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>COCCOC.C(OCC)(=O)C.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.O>[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[C:2]1[N:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[S:5][C:6]=1[C:7]#[N:8]

참가 물질

9

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 592500134-Chloro-2-morpholin-4-yl-1,3-thiazole-5-carbonitrile

생성물 1

HCID 592500334-(2,4-Dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carbonitrile수율 15.2%

시약·촉매·용매 4

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

4-chloro-2-morpholin-4-yl-1,3-thiazole-5-carbonitrile (0.200 g, 0.871 mmol), 2,4-dichlorophenylboronic acid (0.249 g, 1.31 mmol), bis(triphenylphosphine)palladium dichloride (0.061 g, 0.0871 mmol), sodium carbonate (0.184 g, 1.74 mmol) were taken up in DME (3 mL), ethanol (1 mL) and water (1 mL) and microwaved at 125° for 30 minutes. Mixture was diluted with ethyl acetate (10 mL) and extracted. The organic phase was dried with sodium sulfate, filtered and evaporated. ISCO purification on silica gel using 10% ethyl acetate in hexane to 50% ethyl acetate in hexane afforded the title compound (45 mg, 15%). LCMS: (FA) ES+, 340. 1H NMR (400 MHz, d6-DMSO) δ: 7.44 (d, 1H), 7.20-7.17 (m, 2H), 3.43-3.28 (m, 4H), 3.16-2.93 (m, 4H).

후처리

  1. extractionextracted
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customISCO purification on silica gel using 10% ethyl acetate in hexane to 50% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-5f2d6339fad444efbceab5955dabcc84
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183240B2

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