Bromine → 3-Bromothieno[2,3-d]pyridazine
Reaction equation
[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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
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.
Workup
- customirradiated under microwave
- concentrationThe reaction mixture was concentrated in vacuo
- customPurification by ISCO chromatography (1 to 15% methanol:dichloromethane)
Sources & evidence
- ORD record
- ord-d6fd40bf93684d72a4434ce55328ba4b
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08378104B2
Reaction notes
Loading…