Hydrochloric Acid → (5-Bromo-pyridin-2-yl)-(6-trifluoromethyl-pyridin-3-yl)-amine

HRID 76044

反応式

HRID 76044 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.[Br:12][C:13]1[CH:14]=[CH:15][C:16](F)=[N:17][CH:18]=1.Cl>C(O)CCC>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([NH:1][C:2]2[CH:7]=[N:6][C:5]([C:8]([F:11])([F:9])[F:10])=[CH:4][CH:3]=2)=[N:17][CH:18]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 27377445-Amino-2-(trifluoromethyl)pyridineHCID 27831685-Bromo-2-fluoropyridine

生成物 1

HCID 66615754(5-Bromo-pyridin-2-yl)-(6-trifluoromethyl-pyridin-3-yl)-amine

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
150 °C

実験手順

A mixture of 5-amino-2-(trifluoromethyl)pyridine (0.5 g, 3.0 mmol, 1.0 equiv) and 5-bromo-2-fluoropyridine (0.47 mL, 4.6 mmol, 1.5 equiv) in 2 mL 1-butanol was charged with 0.15 mL of 4.0 M HCl (in dioxane) and heated to 150° C. via microwave heating. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and saturated bicarbonate, and the organic extracts were washed with brine and dried over sodium sulphate. Purification of the crude product by flash chromatography afforded the title compound: 1H NMR (400 MHz, CDCl3) δ 6.63 (br. s., 1H) 6.67 (d, J=9.35 Hz, 1H) 7.56 (d, J=8.59 Hz, 1H) 7.62 (dd, J=8.84, 2.53 Hz, 1H) 8.22-8.66 (m, 2H) 8.57 (d, J=2.78 Hz, 1H); (M+H)+320.0.

後処理

  1. temperatureheating
  2. temperatureAfter cooling to room temperature
  3. customthe reaction mixture was partitioned between ethyl acetate and saturated bicarbonate
  4. washthe organic extracts were washed with brine
  5. dry with materialdried over sodium sulphate
  6. customPurification of the crude product by flash chromatography

出典と根拠

ORDレコード
ord-1bb625d4c3f34e6aaf88132922120a2e
出典データセット
uspto-grants-2014_09
特許番号
US08835451B2

関連ノート

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