Phosphorus oxychloride → 3-Bromo-7-chloro-2-methylthieno[2,3-c]pyridine

HRID 2092326ノート

反応式

HRID 2092326 の反応式
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][N+:7]([O-])=[CH:8][CH:9]=2)[S:4][C:3]=1[CH3:12].P(Cl)(Cl)([Cl:15])=O>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:10]2[C:5](=[C:6]([Cl:15])[N:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[CH3:12]

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 673397463-bromo-2-methylthieno[2,3-c]pyridine-N-Oxide

生成物 1

HCID 584664573-Bromo-7-chloro-2-methylthieno[2,3-c]pyridine

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
70 °C

実験手順

3-Bromo-2-methylthieno[2,3-c]pyridine-N-Oxide (0.500 g, 2.05 mmol) was dissolved in chloroform (10 mL) and treated with phosphorous oxychloride (0.955 ml, 10.2 mmol). The reaction was heated to 70° C. while stirring. After 3 hours, the volatiles were removed in vacuo and the residual phosphorous oxychloride was azeotroped with toluene. The resulting residue was taken up in DCM and washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel using a gradient of 20-60% EtOAc in hexanes to give 3-bromo-7-chloro-2-methylthieno[2,3-c]pyridine as a yellow solid. MS (M+H)+ 263.

後処理

  1. customthe volatiles were removed in vacuo
  2. customthe residual phosphorous oxychloride was azeotroped with toluene
  3. washwashed (2×) with an aqueous saturated solution of sodium bicarbonate
  4. dry with materialThe organic layer was then dried with sodium sulfate
  5. custompurified by column chromatography on silica gel using a gradient of 20-60% EtOAc in hexanes

出典と根拠

ORDレコード
ord-1d7faacde16b4c30a674659a5ebf7ff4
出典データセット
uspto-grants-2013_05
特許番号
US08440674B2

反応ノート

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