Toluene → tert-butyl methyl(1-(4-(1-methyl-1H-pyrazol-5-yl)phthalazin-1-yl)piperidin-4-yl)carbamate

HRID 2389245노트

반응식

HRID 2389245 반응식
C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:23][CH2:22][CH:21]([N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][CH2:19]2)=[N:10][N:9]=1.[CH3:33][N:34]1[C:38](B2OC(C)(C)C(C)(C)O2)=[CH:37][CH:36]=[N:35]1.C1(C)C=CC=CC=1>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[CH3:32][N:24]([CH:21]1[CH2:22][CH2:23][N:18]([C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8]([C:38]3[N:34]([CH3:33])[N:35]=[CH:36][CH:37]=3)=[N:9][N:10]=2)[CH2:19][CH2:20]1)[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28]

참가 물질

9

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 49129081-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 58157124tert-Butyl 1-(4-chlorophthalazin-1-yl)piperidin-4-yl(methyl)carbamate

생성물 1

HCID 59627389tert-butyl methyl(1-(4-(1-methyl-1H-pyrazol-5-yl)phthalazin-1-yl)piperidin-4-yl)carbamate수율 1,261.5%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Place sodium carbonate (3.82 g, 36.09 mmol), tert-butyl 1-(4-chlorophthalazin-1-yl)piperidin-4-yl(methyl)carbamate (6.8 g, 18.04 mmol) and 1-methyl-1H-pyrazole-5-boronic acid pinacol ester (5.63 g, 27 1 mmol) in a flask with a mixture of toluene (50 mL), ethanol (17 mL), and water (17 mL). Degas the mixture for 10 min with nitrogen gas. Add tetrakis(triphenylphosphine)palladium (0.4 g, 0.35 mmol) and heat the mixture at 74° C. overnight. Cool the mixture to ambient temperature and dilute with dichloromethane. Wash the organic portion with brine, dry over Na2SO4, and concentrate under reduced pressure. Purify the resulting residue by flash silica gel chromatography (hexane:ethyl acetate:2 M NH3 in MeOH=20:5:1) to provide the title compound as a yellow foam (5.33 g, 70%). ES/MS m/z 423.2 (M+1).

후처리

  1. customDegas the mixture for 10 min with nitrogen gas
  2. washWash the organic portion with brine
  3. dry with materialdry over Na2SO4
  4. concentrationconcentrate under reduced pressure
  5. customPurify the resulting residue by flash silica gel chromatography (hexane:ethyl acetate:2 M NH3 in MeOH=20:5:1)

출처 및 근거

ORD 기록
ord-85ca032435f24000ad06466026993405
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273742B2

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