Cesium fluoride → 6-[5-(6-Chloro-2-methylpyridin-3-yl)-2-ethylphenyl]-2,2,4,4-tetramethylcyclohexane-1,3,5-trione

HRID 1191585노트

반응식

HRID 1191585 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:21][CH3:22])=[C:6]([CH:8]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[C:11](=[O:17])[C:10]([CH3:19])([CH3:18])[C:9]2=[O:20])[CH:7]=1.[F-].[Cs+].[Cl:25][C:26]1[N:31]=[C:30]([CH3:32])[C:29](B(O)O)=[CH:28][CH:27]=1>ClCCl.O>[Cl:25][C:26]1[N:31]=[C:30]([CH3:32])[C:29]([C:2]2[CH:3]=[CH:4][C:5]([CH2:21][CH3:22])=[C:6]([CH:8]3[C:13](=[O:14])[C:12]([CH3:15])([CH3:16])[C:11](=[O:17])[C:10]([CH3:19])([CH3:18])[C:9]3=[O:20])[CH:7]=2)=[CH:28][CH:27]=1

참가 물질

6

반응물 3

HCID 25953Cesium fluorideHCID 441191526-Chloro-2-methylpyridine-3-boronic acidHCID 684845366-(5-Bromo-2-ethylphenyl)-2,2,4,4-tetramethylcyclohexane-1,3,5-trione

생성물 1

HCID 866443106-[5-(6-Chloro-2-methylpyridin-3-yl)-2-ethylphenyl]-2,2,4,4-tetramethylcyclohexane-1,3,5-trione수율 36.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 6-(5-bromo-2-ethylphenyl)-2,2,4,4-tetramethylcyclohexane-1,3,5-trione (0.19 g, 0.5 mmol), cesium fluoride (0.24 g, 1.6 mmol), 6-chloro-2-methylpyridin-3-ylboronic acid (0.13 g, 0.8 mmol) and degassed 1,2-dimethoxyethane (1.7 ml) is stirred under nitrogen at room temperature for 30 minutes. [1,1′-Bis-(diphenylphosphino)ferrocene]dichloro-palladium(II) (0.034 g, 0.042 mmol) is added and the mixture is stirred at room temperature for 10 minutes and then heated at 80° C. overnight. After cooling to room temperature the reaction mixture is diluted with dichloromethane (5 ml) and water and filtered through diatomaceous earth. The filtrate is acidified with 2M aqueous hydrochloric acid, and the organic phase is separated, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is dissolved in N,N-dimethylformamide (approximately 1 ml) and purified by preparative reverse phase HPLC to afford 6-[5-(6-chloro-2-methylpyridin-3-yl)-2-ethylphenyl]-2,2,4,4-tetramethylcyclohexane-1,3,5-trione as a pale brown solid (75.3 mg).

후처리

  1. customdegassed 1,2-dimethoxyethane (1.7 ml)
  2. stirringthe mixture is stirred at room temperature for 10 minutes
  3. temperatureheated at 80° C. overnight
  4. temperatureAfter cooling to room temperature the reaction mixture
  5. filtrationfiltered through diatomaceous earth
  6. customthe organic phase is separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue is dissolved in N,N-dimethylformamide (approximately 1 ml)
  10. custompurified by preparative reverse phase HPLC

출처 및 근거

ORD 기록
ord-5dec77f64af94d1c8a83fcd4b0afd03f
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680012B2

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