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

HRID 2406945노트

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HRID 2406945 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 962Water용매

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온도
80 °C

실험 절차

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, 1 H), 8.51 (d, 1 H), 8.14 (d, 2 H), 7.72 (d, 1 H), 7.65 (d, 2 H).

후처리

  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

출처 및 근거

ORD 기록
ord-e60fab854b7b49e9895fb8c584c1ee01
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809342B2

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