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

HRID 2175073노트

반응식

HRID 2175073 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8028Tetrahydrofuran용매

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온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b4e70e2f73b948d19dc9b5b5a2fb871e
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062015B2

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