3-Aminoquinoline → HCID 57808192, 화합물

HRID 730314

반응식

HRID 730314 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[NH2:18][C:19]1[CH:20]=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOCC.C1(C)C=CC=CC=1>[N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[C:19]([NH:18][C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=3)[CH:5]=[CH:4][N:3]=2)[CH:20]=1

참가 물질

8

반응물 4

HCID 113753-AminoquinolineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 288758632-Chloro-4-(4-trifluoromethylphenyl)pyridine

생성물 1

HCID 57808192HCID 57808192, 화합물

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

반응 조건

온도
90 °C

실험 절차

To an oven-dried 50 mL round-bottomed flask were added 2-chloro-4-(4-trifluoromethyl-phenyl)-pyridine (138 mg, 0.54 mmol) and 3-aminoquinoline (Aldrich Chemical Company) (93 mg, 0.64 mmol), followed by anhydrous toluene (45 mL). Nitrogen was bubbled through the above solution via a needle for 1 h. Then palladium acetate (Aldrich Chemical Company) (18 mg, 0.08 mmol) and BINAP (Aldrich Chemical Company) (50 mg, 0.08 mmol) were added to the reaction in one portion, followed by sodium tert-butoxide (Aldrich Chemical Company) (145 mg, 1.5 mmol). The reaction mixture was heated at 90° C. overnight. After cooling to room temperature, the reaction mixture was taken up to ether, and washed with brine. The aqueous layer was extracted with ether (2×) and the combined ether layer was dried over Na2SO4 and concentrated. The residue was purified on a Biotage 40 S column (2.5:1 hexane:EtOAc) to give the title compound as an off-white solid. MS (ESI, pos. ion) m/z: 366 (M+1). Mp: 207.4-207.5° C.

후처리

  1. customNitrogen was bubbled through the above solution via a needle for 1 h
  2. temperatureAfter cooling to room temperature
  3. washwashed with brine
  4. extractionThe aqueous layer was extracted with ether (2×)
  5. dry with materialthe combined ether layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified on a Biotage 40 S column (2.5:1 hexane:EtOAc)

출처 및 근거

ORD 기록
ord-6e358aab378e45fd9115b72342cafc8b
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582657B2

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