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

HRID 1057036ノート

反応式

HRID 1057036 の反応式
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

参加物

4

反応物 3

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

生成物 1

HCID 672825704-(Difluoromethyl)pyridin-2-amine収率 99.2%

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1351daa0380c4760913980a072d33aef
出典データセット
uspto-grants-2016_07
特許番号
US09399636B2

反応ノート

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