6-Bromo-1-fluoronaphthalen-2-OL → 2-(6,7-Dimethoxy-4-quinolyloxy)-6-bromo-1-fluoronaphthalene

HRID 1925245노트

반응식

HRID 1925245 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2OC1C=C2C(=CC=1)C=C(NC(OCC1C=CC=CC=1)=O)C=C2.[Br:37][C:38]1[CH:39]=[C:40]2[C:45](=[CH:46][CH:47]=1)[C:44]([F:48])=[C:43]([OH:49])[CH:42]=[CH:41]2>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:49][C:43]1[CH:42]=[CH:41][C:40]2[C:45](=[CH:46][CH:47]=[C:38]([Br:37])[CH:39]=2)[C:44]=1[F:48]

참가 물질

6

반응물 2

HCID 112419406-Bromo-1-fluoronaphthalen-2-OLHCID 59813732n-[6-(6,7-Dimethoxy(4-quinolyloxy))(2-naphthyl)](phenylmethoxy)carboxamide

생성물 1

HCID 675205642-(6,7-Dimethoxy-4-quinolyloxy)-6-bromo-1-fluoronaphthalene

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
180 °C

실험 절차

A mixture of 4-chloro-6,7-dimethoxy-quinoline (prepared as in Example 1, Step b)(371 mg, 1.66 mmol), 6-bromo-1-fluoro-naphthalen-2-ol (Step a, 400 mg, 1.66 mmol) and DMAP (203 mg, 1.66 Aldrich) in toluene (in a microwave tube) was heated in a microwave oven (Personal Chemistry, Emrys Optimizer) at 180° C. for 2 h. The mixture was cooled to RT and diluted with 30 mL of EtOAc. The solution was washed with 10 mL of brine twice, dried over Na2SO4 and concentrated in vacuo. The residue was further purified with silica gel column chromatography (40-100% EtOAc in hexanes) to give title compound as a white solid. MS (ESI, pos. ion) m/z: 428.0 (M+1). Mass Calc'd for C21H15BrFNO3: 427.02.

후처리

  1. temperatureThe mixture was cooled to RT
  2. washThe solution was washed with 10 mL of brine twice
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was further purified with silica gel column chromatography (40-100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-a425f14724fb463582e6e94f222ea4d7
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178557B2

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