Potassium Carbonate → 6-Chloro-4-ethoxy-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy)phenyl)quinoline

HRID 1908995노트

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HRID 1908995 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([CH3:14])[C:6](I)=[C:5]2[O:16][CH2:17][CH3:18].[F:19][C:20]([F:39])([F:38])[O:21][C:22]1[CH:37]=[CH:36][C:25]([O:26][C:27]2[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=2)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([CH3:14])[C:6]([C:30]1[CH:29]=[CH:28][C:27]([O:26][C:25]3[CH:36]=[CH:37][C:22]([O:21][C:20]([F:19])([F:38])[F:39])=[CH:23][CH:24]=3)=[CH:32][CH:31]=1)=[C:5]2[O:16][CH2:17][CH3:18]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 56776567{4-[4-(Trifluoromethoxy)phenoxy]phenyl}boronic acidHCID 670163176-Chloro-4-ethoxy-3-iodo-7-methoxy-2-methylquinoline

생성물 1

HCID 670163156-Chloro-4-ethoxy-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy)phenyl)quinoline수율 57%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

To a solution of 6-chloro-4-ethoxy-3-iodo-7-methoxy-2-methylquinoline (1.56 g, 4.13 mmol), (4-(4-(trifluoromethoxy)phenoxy)phenyl)boronic acid (1.85 g, 6.20 mmol) and palladium (0) tetrakis triphenylphosphine (239 mg, 0.207 mmol) in degassed dimethylformamide was added 8.25 ml of a 2 N aqueous potassium carbonate solution. The reaction mixture was stirred 18 hours at 85° C., filtered through celite and concentrated in vacuo. The resulting residue was resuspended in dichloromethane and water. The organic layer was extracted with brine, dried over magnesium sulfate and concentrated in vacuo. Purification by silica gel chromatography (0-20% ethyl acetate in dichloromethane) provided 1.18 g 6-chloro-4-ethoxy-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy)phenyl)quinoline (57% yield) as a light brown solid. 1H NMR (400 MHz, CDCl3) δ 8.11 (s, 1H), 7.43 (s, 1H), 7.31-7.36 (m, 2H), 7.22-7.26 (m, 2H), 7.07-7.14 (m, 4H), 4.04 (s, 3H), 3.71 (q, J=7.1 Hz, 2H), 2.49 (s, 3H), 1.18 (t, J=7.1 Hz, 3H).

후처리

  1. filtrationfiltered through celite and
  2. concentrationconcentrated in vacuo
  3. extractionThe organic layer was extracted with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography (0-20% ethyl acetate in dichloromethane)

출처 및 근거

ORD 기록
ord-90150c1cfc634288b5de637e9e60f0af
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598354B2

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