Bromine → Ethyl 4-amino-2-bromo-6-methylthieno[2,3-b]pyridine-5-carboxylate

HRID 573586ノート

反応式

HRID 573586 の反応式
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[S:14][CH:15]=[CH:16][C:3]=12.[Br:17]Br>C(O)(=O)C>[NH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[S:14][C:15]([Br:17])=[CH:16][C:3]=12

参加物

4

反応物 2

HCID 24408BromineHCID 68323805Ethyl 4-amino-6-methylthieno[2,3-b]pyridine-5-carboxylate

生成物 1

HCID 68323734Ethyl 4-amino-2-bromo-6-methylthieno[2,3-b]pyridine-5-carboxylate収率 87%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a stirred solution of ethyl 4-amino-6-methylthieno[2,3-b]pyridine-5-carboxylate (Description 65) (1 g, 4.23 mmol) in acetic acid (3 mL) was added bromine (0.65 mL, 12.70 mmol) and the resulting mixture stirred at RT overnight (ca. 18 h). The reaction was quenched by pouring the reaction mixture into water and the aqueous solution was basified with NaOH (5M) and diluted with ethyl acetate (30 mL). The organic layer was separated and the aqueous layer was re-extracted with ethyl acetate (20 mL×3). The combined organics were washed with saturated sodium thiosulphate solution, dried and concentrated. Purification by chromatography on silica, eluting with a gradient of 0-30% ethyl acetate in DCM afforded the title compound (1.16 g). LCMS (A) m/z: 315/317 [M+1]+, Rt 0.95 min (acidic).

後処理

  1. customThe reaction was quenched
  2. additionby pouring the reaction mixture into water
  3. additiondiluted with ethyl acetate (30 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was re-extracted with ethyl acetate (20 mL×3)
  6. washThe combined organics were washed with saturated sodium thiosulphate solution
  7. customdried
  8. concentrationconcentrated
  9. customPurification by chromatography on silica
  10. washeluting with a gradient of 0-30% ethyl acetate in DCM

出典と根拠

ORDレコード
ord-e6c1134a44e6478ca606237198ff9971
出典データセット
uspto-grants-2015_05
特許番号
US09029545B2

反応ノート

読み込み中…