Iodine → 3,6-Dichloro-4-iodopyridazine

3,6-Dichloropyridazine (3) (149 mg, 1.0 mmol) in THF (2 mL) was added to a solution of TMPZnCl.LiCl (2) (1.3 M in THF, 0.85 mL, 1.1 mmol) at 25° C. and the reaction mixture was then stirred at this temperature for 30 min according to TP 2. I2 (381 mg, 1.5 mmol) dissolved in dry THF (2 mL) was then dropwise added and the resulting mixture was stirred for 0.5 h. The reaction mixture was quenched with a sat. aq. Na2S2O3 solution (10 mL) and with a sat. aq. NH4Cl solution (20 mL), extracted with diethyl ether (3×50 mL) and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. Purification by flash-chromatography (CH2Cl2/n-pentane, 1:2) furnished compound 5a (231 mg, 84%) as a colourless solid.

1. additionwas then dropwise added
2. customThe reaction mixture was quenched with a sat. aq. Na2S2O3 solution (10 mL) and with a sat. aq. NH4Cl solution (20 mL)
3. extractionextracted with diethyl ether (3×50 mL)
4. dry with materialdried over anhydrous Na2SO4
5. filtrationAfter filtration
6. customthe solvent was evaporated in vacuo
7. customPurification by flash-chromatography (CH2Cl2/n-pentane, 1:2)

ORD record

ord-b68147e940fd4a8293d6bbb20c23b70c

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09334237B2