Bromine → 3-Bromothieno[2,3-d]pyridazine

HRID 389551ノート

反応式

HRID 389551 の反応式
[S:1]1[C:5]2=[CH:6][N:7]=[N:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C([O-])(=O)C.[Na+].[Br:15]Br>C(O)(=O)C>[Br:15][C:3]1[C:4]2[C:5](=[CH:6][N:7]=[N:8][CH:9]=2)[S:1][CH:2]=1

参加物

5

反応物 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 12603003Thieno[2,3-d]pyridazine

生成物 1

HCID 228926363-Bromothieno[2,3-d]pyridazine収率 28.5%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
90 °C

実験手順

A solution of thieno[2,3-d]pyridazine (468.0 mg, 3.437 mmol) and sodium acetate (879.2 mg, 10.50 mmol) in acetic acid (14 mL) was charged with bromine (0.55 mL, 11 mmol) and then irradiated under microwave heating at 90° C. for 3 h. The reaction mixture was concentrated in vacuo. Purification by ISCO chromatography (1 to 15% methanol:dichloromethane) afforded 210.6 mg (27%) of the title compound as a pink solid. 1H NMR (400 MHz, DMSO-d6): δ 9.96 (d, J=1.52 Hz, 1H), 9.53 (d, J=1.52 Hz, 1H), 8.51 (s, 1H); MS (ESI): 214.97, 216.92 [M+H]+; HPLC tR=2.68 min.

後処理

  1. customirradiated under microwave
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customPurification by ISCO chromatography (1 to 15% methanol:dichloromethane)

出典と根拠

ORDレコード
ord-d6fd40bf93684d72a4434ce55328ba4b
出典データセット
uspto-grants-2013_02
特許番号
US08378104B2

反応ノート

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