Potassium Carbonate → 5-Nitro-2-(4-(trifluoromethyl)phenyl)pyridine

HRID 1427449ノート

反応式

HRID 1427449 の反応式
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Cl[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=2)=[N:16][CH:17]=1)([O-:23])=[O:22]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 783082-Chloro-5-nitropyridineHCID 27343894-(Trifluoromethyl)phenylboronic acid

生成物 1

HCID 679808515-Nitro-2-(4-(trifluoromethyl)phenyl)pyridine収率 37%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

4-(trifluoromethyl)phenylboronic acid (500 mg, 2.63 mmol), 2-chloro-5-nitropyridine (417 mg, 2.63 mmol), potassium carbonate (908 mg, 6.58 mmol) and palladium(II) acetate (23.6 mg, 0.105 mmol) were combined in 1:1 dioxane:water (10 mL). The resulting mixture was stirred at 80° C. for 12 hours. The mixture was filtered and the solution was extracted with ethyl acetate. The organic layer was washed with water, then brine, dried over sodium sulfate, filtered and concentrated. Purification by column chromatography gave 5-nitro-2-(4-(trifluoromethyl)phenyl)pyridine (260 mg, 37%). 1H NMR (400 MHz, CDCl3, δ): 9.47 (s, 1H), 8.51 (d, 1H), 8.14 (d, 2H), 7.72 (d, 1H), 7.65 (d, 2H).

後処理

  1. filtrationThe mixture was filtered
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialbrine, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography

出典と根拠

ORDレコード
ord-581300d2d8c040a7a29bff58f8313c41
出典データセット
uspto-grants-2015_01
特許番号
US08933104B2

反応ノート

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