Potassium Phosphate, Tribasic → 1-[2-Methyl-5-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-phenyl]piperazine

HRID 2175073ノート

反応式

HRID 2175073 の反応式
Cl[C:2]1[CH:3]=[CH:4][C:5]([CH3:14])=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=1.CC1(C)C(C)(C)OB([C:23]2[CH:32]=[CH:31][C:30]3[C:29]([CH3:34])([CH3:33])[CH2:28][CH2:27][C:26]([CH3:36])([CH3:35])[C:25]=3[CH:24]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:14][C:5]1[CH:4]=[CH:3][C:2]([C:32]2[CH:23]=[CH:24][C:25]3[C:26]([CH3:36])([CH3:35])[CH2:27][CH2:28][C:29]([CH3:34])([CH3:33])[C:30]=3[CH:31]=2)=[CH:7][C:6]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 693767N-(5-Chloro-2-methylphenyl)piperazineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 112439294,4,5,5-Tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane

生成物 1

HCID 532523231-[2-Methyl-5-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-phenyl]piperazine

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
120 °C

実験手順

100 mg (0.48 mmol) of 1-(5-chloro-2-methylphenyl)piperazine and 300 mg (0.95 mmol) and of 4,4,5,5-tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane are dissolved in 2 ml of THF, 302 mg (1.43 mmol) of potassium phosphate, 3 mg of palladium acetate and 11 mg of 2-dicylcohexylphosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl are added. The reaction mixture is degassed a number of times and stirred at 120° C. under nitrogen atmosphere for 4 h, subsequently diluted with water and extracted three times with ethyl acetate. The combined organic phases are dried over Na2SO4 and evaporated. The crude product is purified by means of preparative HPLC and converted into the hydrochloride using methanolic HCl.

後処理

  1. customThe reaction mixture is degassed a number of times
  2. additionsubsequently diluted with water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. customevaporated
  6. customThe crude product is purified by means of preparative HPLC

出典と根拠

ORDレコード
ord-b4e70e2f73b948d19dc9b5b5a2fb871e
出典データセット
uspto-grants-2015_06
特許番号
US09062015B2

反応ノート

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