Potassium tert-butoxide → 2-Chloro-4-(4-methyl-6-nitropyridin-3-yloxy)pyridine

HRID 2060706

反応式

HRID 2060706 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][N:3]=1.CC(C)([O-])C.[K+].Br[C:16]1[C:17]([CH3:25])=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[N:20][CH:21]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:16]2[CH:21]=[N:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=2[CH3:25])[CH:5]=[CH:4][N:3]=1

参加物

6

反応物 3

HCID 23665647Potassium tert-butoxideHCID 533503725-Bromo-4-methyl-2-nitropyridineHCID 178516507HCID 178516507、化合物

生成物 1

HCID 866416892-Chloro-4-(4-methyl-6-nitropyridin-3-yloxy)pyridine収率 18%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
65 °C

実験手順

2-Chloro-4-hydroxypyridine (0.239 g, 1.843 mmol) was dissolved in DMF (18.43 ml) and potassium t-butoxide (0.290 g, 2.58 mmol) was added. The solution was degassed for several minutes, and then 5-bromo-4-methyl-2-nitropyridine (0.4 g, 1.843 mmol) was added. The mixture was heated at 65° C. for 70 hours under argon and then at 80° C. for 24 hours. The reaction mixture was cooled to RT, diluted with ethyl acetate (150 mL), washed with water (75 mL), 10% aqueous LiCl (2×75 mL), saturated aqueous bicarbonate (75 mL) and brine (75 mL), dried (MgSO4), evaporated and purified via silica gel chromatography (ethyl acetate/hexanes) to yield 2-chloro-4-(4-methyl-6-nitropyridin-3-yloxy)pyridine as a yellow solid (0.087 g, 18% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.49 (s, 1H), 8.47 (s, 1H), 8.35 (d, 1H), 7.24 (d, 1H), 7.12 (dd, 1H), 2.31 (s, 3H); MS (ESI) m/z: 266.0 (M+H+).

後処理

  1. customThe solution was degassed for several minutes
  2. temperatureThe reaction mixture was cooled to RT
  3. washwashed with water (75 mL), 10% aqueous LiCl (2×75 mL), saturated aqueous bicarbonate (75 mL) and brine (75 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. custompurified via silica gel chromatography (ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-04b09225a1e343819660f092fde3347b
出典データセット
uspto-grants-2012_10
特許番号
US08278331B2

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