Phosphorus oxychloride → 3-Bromo-4-chlorothieno(3,2-c)pyridine

HRID 17117ノート

反応式

HRID 17117 の反応式
[Br:1][C:2]1[C:6]2[C:7](=O)[NH:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.O=P(Cl)(Cl)[Cl:14]>>[Br:1][C:2]1[C:6]2[C:7]([Cl:14])=[N:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 184507963-Bromothieno[3,2-c]pyridin-4(5H)-one

生成物 1

HCID 184507733-Bromo-4-chlorothieno(3,2-c)pyridine

実験手順

A suspension of Example 1A (35.91 g, 0.156 mol) in POCl3 (80 mL) was heated to reflux for 2.5 hours, cooled to room temperature, poured onto 800 g of ice, and extracted repeatedly with dichloromethane. The combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography on silica gel with 0 to 5% methanol/dichloromethane to provide 29.3 g of 3-bromo-4-chlorothieno[3,2-c]pyridine (mp 158-159° C.), which was diluted with dioxane (500 mL) and concentrated aqueous NH3 (500 mL), heated to 150° C. under pressure (260 psi) for 20 hours, and concentrated. The residue was triturated from MTBE then from methanol to provide 20.29 g of the desired product. m.p. 153-155° C.

後処理

  1. temperatureto reflux for 2.5 hours
  2. extractionextracted repeatedly with dichloromethane
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel with 0 to 5% methanol/dichloromethane

出典と根拠

ORDレコード
ord-8c3a03bcf48d44bd99fd4b8546a10541
出典データセット
uspto-grants-2010_06
特許番号
US07737160B2

反応ノート

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