Cesium carbonate → 6-[2-(2,5-Dichlorophenyl)-5-methylthiazol-4-yl]-2,2,4,4-tetramethylcyclohexane-1,3,5-trione

HRID 1849962노트

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HRID 1849962 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1B(O)O.BrC1SC(C[O:19][C:20]2[C:25]([CH3:27])([CH3:26])[C:24](=[O:28])[C:23]([CH3:30])([CH3:29])[C:22](=[O:31])[CH:21]=2)=CN=1.C(=O)([O-])[O-].[Cs+].[Cs+].[N-](S(C(F)(F)F)(=O)=O)[S:39](C(F)(F)F)(=O)=O.[CH2:53]([N+:57]1[CH:61]=CN(C)C=1)[CH2:54][CH2:55]C>COCCOCCOC.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:61]1[S:39][C:54]([CH3:55])=[C:53]([CH:21]2[C:22](=[O:31])[C:23]([CH3:29])([CH3:30])[C:24](=[O:28])[C:25]([CH3:26])([CH3:27])[C:20]2=[O:19])[N:57]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 27733712,5-Dichlorobenzeneboronic acidHCID 59562431HCID 59562431, 화합물HCID 1784485511-Butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide

생성물 1

HCID 595624336-[2-(2,5-Dichlorophenyl)-5-methylthiazol-4-yl]-2,2,4,4-tetramethylcyclohexane-1,3,5-trione

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8150Diglyme용매

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온도
150 °C

실험 절차

2,5-dichlorophenylboronic acid (266 mg, 1.39 mmol), 5-(2-bromothiazol-5-ylmethoxy)-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione (250 mg, 0.7 mmol), toluene (3 ml), caesium carbonate (310 mg, 0.95 mmol) and [1,3-bis(2,6-diisopropyl)imidazol-2-ylidene](3-chloropyridyl)palladium II dichloride (60 mg, 0.12 mmol) are mixed together in a microwave vial and heated to 150° C. for 30 min under microwave irradiation. The reaction mixture is cooled, filtered, evaporated and purified by flash chromatography on silica gel to give an orange oil. The oil is dissolved in diglyme (3 ml) and 1-butyl-3-methyl imidazolium bis(trifluoromethylsulfonyl)imide (0.1 ml) and heated under microwave irradiation at 210° C. for 30 min. The reaction mixture is cooled to room temperature, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 6-[2-(2,5-dichlorophenyl)-5-methylthiazol-4-yl]-2,2,4,4-tetramethylcyclohexane-1,3,5-trione.

후처리

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. customevaporated
  4. custompurified by flash chromatography on silica gel
  5. customto give an orange oil
  6. temperatureThe reaction mixture is cooled to room temperature
  7. customthe solvent is evaporated under reduced pressure
  8. customthe residue is purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-ed2c7bc668d042bea14677a1bc283784
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08956999B2

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