2,6-Di-tert-butyl-4-methylphenol → 4-(4-Vinyl-5-isoquinolyl)amino-1-(tert-butoxycarbonyl)piperidine

HRID 1373064

반응식

HRID 1373064 반응식
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:5]=[N:4][CH:3]=1.[CH2:26](C([Sn])=C(CCCC)CCCC)[CH2:27]CC.C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)(C)(C)C.[F-].[K+]>C1(C)C=CC=CC=1.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>[CH:26]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:5]=[N:4][CH:3]=1)=[CH2:27]

참가 물질

7

반응물 4

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 522689Potassium FluorideHCID 219799724-(4-Bromo-5-isoquinolyl)amino-1-(tert-butoxycarbonyl)piperidineHCID 53438229Tri(butyl)vinyltin

생성물 1

HCID 219799424-(4-Vinyl-5-isoquinolyl)amino-1-(tert-butoxycarbonyl)piperidine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

A suspension of Intermediate 6 (8.00 g), tri(n-butyl)vinyltin (8.63 ml), tetrakis(triphenylphosphine)palladium(0) (455 mg), and 2,6-di-tert-butyl-p-cresol (8.7 mg) in toluene (120 ml) was stirred at 110° C. for 2 hours. The reaction mixture was cooled to room temperature, then added with 10% aqueous potassium fluoride (120 ml), and stirred for 15 hours. After the precipitates were removed by filtration, the organic layer was separated, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the title compound (6.72 g).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringstirred for 15 hours
  3. customAfter the precipitates were removed by filtration
  4. customthe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-fdeb0d8ab2bd48f9bf688e687a0f3bb3
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07160894B2

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