3,6-Dichloropyridazine → HCID 14143072, compound

HRID 522501Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[Li+].[Cl-].C([Cu])#N.[F:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1>C1COCC1>[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][C:7]=1[C:19]([C:18]1[CH:22]=[CH:23][C:15]([F:14])=[CH:16][CH:17]=1)=[O:20]

Participants

Conditions

Temperature: -20 °C

Procedure

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. After cooling down to −20° C., CuCN.2LiCl (1.0 M in THF, 1.1 mmol, 1.1 equiv) was added and the resulting mixture was stirred for 30 min at this temperature. 4-Fluorobenzoyl chloride (317 mg, 2.0 mmol) was then slowly added and the resulting mixture was allowed to warm up slowly to 10° C. The reaction mixture was quenched 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, 1:1) furnished compound 5b (259 mg, 96%) as a white solid.

Workup

temperatureto warm up slowly to 10° C
customThe reaction mixture was quenched with a sat. aq. NH4Cl solution (20 mL)
extractionextracted with diethyl ether (3×50 mL)
dry with materialdried over anhydrous Na2SO4
filtrationAfter filtration
customthe solvent was evaporated in vacuo
customPurification by flash-chromatography (CH2Cl2/n-pentane, 1:1)

Sources & evidence

ORD record: ord-d4012b8b41a6411ca52358db9b1cce57
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334237B2

Reaction notes

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