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

HRID 1431008ノート

反応式

HRID 1431008 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-9bac1b969c4b4219bb8c8e7c0c013dc6
出典データセット
uspto-grants-2015_01
特許番号
US08940927B2

反応ノート

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