Hydrochloric Acid → HCID 68481886, 화합물

HRID 1470893노트

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HRID 1470893 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1B(O)O.Br[C:13]1[CH:14]=[CH:15][C:16]([CH2:32][CH3:33])=[C:17]([CH:19]2[C:24](=[O:25])[C:23]([CH3:27])([CH3:26])[C:22](=[O:28])[C:21]([CH3:30])([CH3:29])[C:20]2=[O:31])[CH:18]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl>ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Na].[Na].[Na].S(C1C=C(P(C2C=CC=C(S(O)(=O)=O)C=2)C2C=CC=C(S(O)(=O)=O)C=2)C=CC=1)(O)(=O)=O.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:14]=[CH:15][C:16]([CH2:32][CH3:33])=[C:17]([CH:19]2[C:20](=[O:31])[C:21]([CH3:29])([CH3:30])[C:22](=[O:28])[C:23]([CH3:27])([CH3:26])[C:24]2=[O:25])[CH:18]=1

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, Tribasic2회HCID 2734659(2,4-Dichlorophenyl)boronic acid2회HCID 684845366-(5-Bromo-2-ethylphenyl)-2,2,4,4-tetramethylcyclohexane-1,3,5-trione

생성물 1

HCID 68481886HCID 68481886, 화합물수율 37.4%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 86657037CID 86657037촉매HCID 962Water용매HCID 6344Dichloromethane용매

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온도
160 °C

실험 절차

To a microwave vial is added palladium(II) acetate (1.1 mg, 0.0049 mmol), tris(3-sulfophenyl)phosphine trisodium salt (5.1 mg, 0.0099 mmol), 2,4-dichlorophenylboronic acid (0.099 g, 0.5 mmol), 6-(5-bromo-2-ethylphenyl)-2,2,4,4-tetramethylcyclohexane-1,3,5-trione (0.19 g, 0.5 mmol) and potassium phosphate (0.53 g, 2.5 mmol). Degassed water (0.75 ml) is next added (washing-down any solids from the slides of the vial), followed by stirring for 5 minutes and flushing with argon. This mixture is then heated at 160° C. under microwave irradiation for 15 minutes. A further quantity of 2,4-dichlorophenylboronic acid (0.099 g, 0.5 mmol) and potassium phosphate (0.095 g, 0.5 mmol) are added, the reaction mixture again blanketed under an atmosphere of argon, and the mixture is heated at 160° C. for a further 15 minutes. After cooling to room temperature the reaction mixture is diluted with dichloromethane (5 ml) and acidified with 2M aqueous hydrochloric acid. The organic phase is separated, dried over anhydrous magnesium sulfate, and filtered through a plug of silica gel. The filtrate is concentrated under reduced pressure and the residue is dissolved in N,N-dimethylformamide (approximately 1 ml) and purified by preparative reverse phase HPLC to afford 6-(2′,4′-dichloro-4-ethylbiphenyl-3-yl)-2,2,4,4-tetramethyl-cyclohexane-1,3,5-trione as a colourless oil (80.6 mg).

후처리

  1. washwashing-down any solids from the slides of the vial),
  2. customflushing with argon
  3. temperaturethe mixture is heated at 160° C. for a further 15 minutes
  4. temperatureAfter cooling to room temperature the reaction mixture
  5. customThe organic phase is separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered through a plug of silica gel
  8. concentrationThe filtrate is concentrated under reduced pressure
  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-e86fa4106ae64c74952452bcbdbf4074
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006429B2

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