Water → N-(2-nitropyridin-3-yl)pyridin-2-amine

HRID 2036624

反応式

HRID 2036624 の反応式
F[C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.CC(C)([O-])C.[K+].O>CN(C=O)C>[N+:8]([C:3]1[C:2]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)([O-:10])=[O:9]

参加物

6

反応物 4

HCID 962WaterHCID 104392-AminopyridineHCID 27628023-Fluoro-2-nitropyridineHCID 23665647Potassium tert-butoxide

生成物 1

HCID 58459246N-(2-nitropyridin-3-yl)pyridin-2-amine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-fluoro-2-nitropyridine (3.32 g, 23.38 mmol) and 2-aminopyridine (2.0 g, 21.25 mmol) in DMF (35.4 mL) was added potassium tert-butoxide (4.77 g, 42.5 mmol). The solution was stirred under nitrogen at rt overnight. After 22 h, the mixture was poured into water (100 mL) and extracted with EtOAc (2×100 mL). After drying with MgSO4, the solution was filtered and concentrated in vacuo to provide the crude material as a orange solid. The orange solid was purified by chromatography through a Redi-Sep™ pre-packed silica gel column (80 g), eluting with a gradient of 0% to 50% EtOAc in hexane, to provide N-(2-nitropyridin-3-yl)pyridin-2-amine as an orange solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 9.53 (1H, s), 8.58 (1H, dd, J=8.4, 1.6 Hz), 8.15 (1H, dd, J=4.3, 1.4 Hz), 8.10-8.14 (1H, m), 7.66-7.76 (2H, m), 7.05 (1H, dt, J=8.4, 0.8 Hz), 6.93 (1H, ddd, J=7.2, 5.0, 0.9 Hz); LC-MS (ESI) m/z 217.0 [M+H]+.

後処理

  1. waitAfter 22 h
  2. extractionextracted with EtOAc (2×100 mL)
  3. dry with materialAfter drying with MgSO4
  4. filtrationthe solution was filtered
  5. concentrationconcentrated in vacuo
  6. customto provide the crude material as a orange solid
  7. customThe orange solid was purified by chromatography through a Redi-Sep™ pre-packed silica gel column (80 g)
  8. washeluting with a gradient of 0% to 50% EtOAc in hexane

出典と根拠

ORDレコード
ord-5634fc11f05848348c514a34560fda03
出典データセット
uspto-grants-2013_11
特許番号
US08575183B2

関連ノート

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