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

HRID 1849962ノート

反応式

HRID 1849962 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8150Diglyme溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ed2c7bc668d042bea14677a1bc283784
出典データセット
uspto-grants-2015_02
特許番号
US08956999B2

反応ノート

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