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

HRID 1925245ノート

反応式

HRID 1925245 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
180 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a425f14724fb463582e6e94f222ea4d7
出典データセット
uspto-grants-2012_05
特許番号
US08178557B2

反応ノート

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