Toluene → Ethyl 2-(2,4-difluorophenyl)pyridine-3-carboxylate

HRID 1257090ノート

反応式

HRID 1257090 の反応式
C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]1[N:18]=[CH:17][CH:16]=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1B(O)O.C1(C)C=CC=CC=1>CCO>[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[C:8]1[N:18]=[CH:17][CH:16]=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

参加物

6

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27343342,4-Difluorophenylboronic acidHCID 2796614Ethyl chloronicotinate

生成物 1

HCID 21062877Ethyl 2-(2,4-difluorophenyl)pyridine-3-carboxylate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
82 °C

実験手順

To a nitrogen purged 3.0 L, 4-necked flask, fitted with an overhead stirrer, thermocouple, heating mantle, nitrogen outlet and reflux condenser, was charged Pd(Ph3)4 (5.0 g, 4.33 mmoles, 0.005 eq), sodium carbonate (92.6 g, 874 mmoles, 1.3 eq), ethyl 2-chloronicotinate, 1 (126.0 g, 678 moles, 1.0 eq), 2,4-difluorophenylboronic acid, 2 (125 g, 791 mmoles, 1.2 eq), followed by 0.5 L of toluene and 125 mL denatured EtOH. The reaction was heated to 82° C. with vigorous stirring under N2 overnight (completeness of reaction determined by HPLC and TLC). The reaction was cooled to room temperature, the mixture filtered through a small pad of Celite® and the solvents removed under vacuum at 55° C. The residue was dissolved in EtOAc, washed, dried (MgSO4), filtered through Celite® again, and concentrated. The product was obtained as a yellow solid.

後処理

  1. customTo a nitrogen purged 3.0 L, 4-necked flask
  2. customfitted with an overhead stirrer
  3. temperaturethermocouple, heating mantle, nitrogen outlet
  4. temperaturereflux condenser
  5. custom(completeness of reaction determined by HPLC and TLC)
  6. temperatureThe reaction was cooled to room temperature
  7. filtrationthe mixture filtered through a small pad of Celite®
  8. customthe solvents removed under vacuum at 55° C
  9. dissolutionThe residue was dissolved in EtOAc
  10. washwashed
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered through Celite® again
  13. concentrationconcentrated
  14. customThe product was obtained as a yellow solid

出典と根拠

ORDレコード
ord-da1825df82e245e29ab66c0720fc03e3
出典データセット
uspto-grants-2013_06
特許番号
US08461345B2

反応ノート

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