Hydrochloric Acid → HCID 68481886、化合物

HRID 1191584ノート

反応式

HRID 1191584 の反応式
[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

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, Tribasic2 回HCID 2734659(2,4-Dichlorophenyl)boronic acid2 回HCID 684845366-(5-Bromo-2-ethylphenyl)-2,2,4,4-tetramethylcyclohexane-1,3,5-trione

生成物 1

HCID 68481886HCID 68481886、化合物収率 37.4%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 86657037CID 86657037触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
160 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-de338d87e4f94b4a8fcc54a993467cfd
出典データセット
uspto-grants-2014_03
特許番号
US08680012B2

反応ノート

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