Trifluoroacetic acid → 4-(Difluoromethyl)pyridin-2-amine

HRID 1057036노트

반응식

HRID 1057036 반응식
C([NH:5][C:6]1[CH:11]=[C:10]([CH:12]([F:14])[F:13])[CH:9]=[CH:8][N:7]=1)(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>>[F:13][CH:12]([F:14])[C:10]1[CH:9]=[CH:8][N:7]=[C:6]([NH2:5])[CH:11]=1

참가 물질

4

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 90015299N-tert-butyl-4-(difluoromethyl)pyridin-2-amine

생성물 1

HCID 672825704-(Difluoromethyl)pyridin-2-amine수율 99.2%

반응 조건

온도
90 °C

실험 절차

A flask containing N-tert-butyl-4-(difluoromethyl)pyridin-2-amine (4.43 g, 22.1 mmol), triethylsilane (7.28 mL, 44.2 mmol) and trifluoroacetic acid (22.1 mL, 1 M) was fitted with a reflux condenser. The reaction mixture was stirred at 90° C. for 21 hr and then, after cooling to rt, concentrated to dryness and partitioned between CH2Cl2 and sat. aq. NaHCO3. After separation of the phases, the aqueous layer was re-extracted with CH2Cl2 and the combined organics were dried over MgSO4. Concentration afforded 4-(difluoromethyl)pyridin-2-amine as a light brown solid (3.16 g, >99%); 1H NMR (400 MHz, CDCl3) δ 8.16 (d, J=5.3 Hz, 1H), 6.74 (d, J=5.3 Hz, 1H), 6.66-6.33 (m, 2H), 4.62 (br s, 2H).

후처리

  1. customwas fitted with a reflux condenser
  2. temperatureafter cooling to rt
  3. concentrationconcentrated to dryness
  4. custompartitioned between CH2Cl2 and sat. aq. NaHCO3
  5. customAfter separation of the phases
  6. extractionthe aqueous layer was re-extracted with CH2Cl2
  7. dry with materialthe combined organics were dried over MgSO4
  8. concentrationConcentration

출처 및 근거

ORD 기록
ord-1351daa0380c4760913980a072d33aef
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399636B2

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