4-Bromophenol → 4-(4-Bromo-phenoxy)-quinoline-2-carboxylic acid ethyl ester

HRID 1431008노트

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HRID 1431008 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14](Cl)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1)=[O:5])[CH3:2].[Br:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]([O:24][C:21]2[CH:22]=[CH:23][C:18]([Br:17])=[CH:19][CH:20]=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1)=[O:5])[CH3:2]

참가 물질

5

반응물 3

HCID 78084-BromophenolHCID 10796Cesium carbonateHCID 269156Ethyl 4-chloroquinoline-2-carboxylate

생성물 1

HCID 585290504-(4-Bromo-phenoxy)-quinoline-2-carboxylic acid ethyl ester수율 42.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To a solution of 4-chloro-quinoline-2-carboxylic acid ethyl ester (910 mg, 3.87 mmol) in DMF (15 ml) was added 4-bromophenol (737 mg, 4.26 mmol), followed by Cs2CO3 (1.89 g, 5.81 mmol). The reaction mixture was then heated to 60° C. for 16 hrs. On the second day the mixture was cooled to r.t. and concentrated down. The residue was partitioned between EtOAc (10 ml) and water (20 ml). The EtOAc layer was separated, dried over MgSO4, filtrated, concentrated, and purified by Biotage with EtOAc/Hexane (15%, 4 CV) to afford 4-(4-bromo-phenoxy)-quinoline-2-carboxylic acid ethyl ester (609 mg, 42.3%). 1H NMR (300 MHz, DMSO-d6): δ 8.36 (m, 1H), 8.18 (m, 1H), 7.93 (m, 1H), 7.80 (m, 1H). 7.75 (m, 2H), 7.34 (m, 2H), 7.14 (s, 1H), 4.34 (m, 2H), 1.30 (m, 3H). LC-MS m/z=373 [C18H14BrNO3+H]+.

후처리

  1. temperatureOn the second day the mixture was cooled to r.t.
  2. concentrationconcentrated down
  3. customThe residue was partitioned between EtOAc (10 ml) and water (20 ml)
  4. customThe EtOAc layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. custompurified by Biotage with EtOAc/Hexane (15%, 4 CV)

출처 및 근거

ORD 기록
ord-9bac1b969c4b4219bb8c8e7c0c013dc6
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940927B2

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