Pyridazine → Ethyl 4-[6-chloro-2-(4-fluorophenyl)-imidazo[1,2-b]pyridazin-3-yl]-4H-pyridazine-1-carboxylate

HRID 515556Notes

Reaction equation

Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[N:16]=2)[N:13]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1>ClCCl>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([C:14]([CH:28]3[CH:27]=[CH:26][N:25]([C:2]([O:4][CH2:5][CH3:6])=[O:3])[N:24]=[CH:29]3)=[C:15]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[N:16]=2)[N:13]=1

Participants

Conditions

Temperature: 10 °C

Procedure

2.90 ml (30.3 mmol) of ethyl chloroformate are added, dropwise in 30 minutes, to a solution of 3.00 g (12.1 mmol) of 6-chloro-2-(4-fluorophenyl)imidazo[1,2-b]pyridazine (CAS: 244081-70-7) and 4.40 ml (60.6 mmol) of pyridazine in 40 ml of dichloromethane at 10° C. The medium is stirred at 10° C. for a further hour and then left to stir for 3 hours. It is then poured into ice-cold water and the product is extracted with ethyl acetate.

Workup

waitleft
stirringto stir for 3 hours
additionIt is then poured into ice-cold water
extractionthe product is extracted with ethyl acetate

Sources & evidence

ORD record: ord-8e7fa7b1880a4635a86e1f0e085bc3c5
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108971B2

Reaction notes

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