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Water → 4-[6-(5,5-Dimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 2175061
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HRID 2175061 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16](Br)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][C:22]1([CH3:41])[CH2:31][CH2:30][CH2:29][C:28]2[CH:27]=[C:26](B3OC(C)(C)C(C)(C)O3)[CH:25]=[CH:24][C:23]1=2.O.O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>COCCO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:26]3[CH:25]=[CH:24][C:23]4[C:22]([CH3:41])([CH3:21])[CH2:31][CH2:30][CH2:29][C:28]=4[CH:27]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

8

반응물 4

HCID 962WaterHCID 160590464-Boc-1-(6-bromo-2-pyridyl)piperazineHCID 18407952Tripotassium phosphate trihydrateHCID 532501122-(5,5-Dimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 672484724-[6-(5,5-Dimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 80192-Methoxyethanol용매HCID 8857Ethyl Acetate용매

실험 절차

500 mg (1.46 mmol) of 4-(6-bromopyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester, 460 mg (1.61 mmol) of 2-(5,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 620 mg (2.92 mmol) of tripotassium phosphate trihydrate are suspended in 10 ml of ethylene glycol monomethyl ether, degassed a number of times, and 82 mg (0.04 mmol) of bis(triphenylphosphine)palladium(II) dichloride are added under nitrogen atmosphere. The reaction mixture is treated in an ultrasound bath for 10 min, subsequently irradiated in the microwave at 100° C. for 90 min, 50 ml of water and 50 ml of ethyl acetate are added, and the mixture is filtered. The residue is discarded. The organic phase of the filtrate is separated off, and the aqueous phase is extracted three times with ethyl acetate. The combined organic phases are dried over Na2SO4 and evaporated. The crude product is purified by means of flash chromatography on silica gel.

후처리

  1. additionare added under nitrogen atmosphere
  2. additionThe reaction mixture is treated in an ultrasound bath for 10 min
  3. customsubsequently irradiated in the microwave at 100° C. for 90 min
  4. filtrationthe mixture is filtered
  5. customThe organic phase of the filtrate is separated off
  6. extractionthe aqueous phase is extracted three times with ethyl acetate
  7. dry with materialThe combined organic phases are dried over Na2SO4
  8. customevaporated
  9. customThe crude product is purified by means of flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-5f504cbfd54b4893bcc02a95d4601278
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09062015B2

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