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Potassium Phosphate, Tribasic → 2-(2,3-Difluoro-6-methoxy-phenyl)-N-methoxy-N-methyl-isonicotinamide

HRID 1909016
ノート
印刷プレビュー

反応式

HRID 1909016 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][N:13]=1)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6].[F:14][C:15]1[C:20]([F:21])=[CH:19][CH:18]=[C:17]([O:22][CH3:23])[C:16]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[F:14][C:15]1[C:20]([F:21])=[CH:19][CH:18]=[C:17]([O:22][CH3:23])[C:16]=1[C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][N:13]=1)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 43727862,3-Difluoro-6-methoxyphenylboronic acidHCID 448186542-Bromo-N-methoxy-N-methylisonicotinamide

生成物 1

HCID 866643432-(2,3-Difluoro-6-methoxy-phenyl)-N-methoxy-N-methyl-isonicotinamide収率 23%

試薬・触媒・溶媒 2

HCID 178418851HCID 178418851、化合物
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

A flask containing 2-bromo-N-methoxy-N-methyl-isonicotinamide (Example 25, using method 2) (3.0 g, 12.2 mmol) 2,3-difluoro-6-methoxyphenylboronic acid (4.6 g, 24.4 mmol)) and 2M aqueous K3PO4 (15 mL, 30.6 mmol) in 1,4-dioxane (40 mL) was successively evacuated and flushed with nitrogen. Pd(PtBu3)2 (268 mg, 0.48 mmol) was then added and the mixture heated at 90° C. for 2 hours. The mixture was cooled, concentrated in vacuo and then partitioned between EtOAc and sat. aqueous NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by SiO2 chromatography (eluting with 30-100% EtOAc/hexane) gave the title compound (0.856 g, 23%). MS(ESI) m/z 309 (M+H)+

後処理

  1. customwas successively evacuated
  2. customflushed with nitrogen
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated in vacuo
  5. custompartitioned between EtOAc and sat. aqueous NaHCO3 solution
  6. washThe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customPurification
  10. washby SiO2 chromatography (eluting with 30-100% EtOAc/hexane)

出典と根拠

ORDレコード
ord-8eaede80015a49b7976a59d2cffffad1
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08598217B2

反応ノート

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