Chlorosuccinimide → Ethyl 2-benzyl-7-chloro-4-(4-fluorophenyl)pyrrolo[1,2-b]pyridazine-3-carboxylate

HRID 2250576Notes

Reaction equation

[CH2:1]([C:8]1[C:9]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:10]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:11]2[N:12]([CH:14]=[CH:15][CH:16]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:29]N1C(=O)CCC1=O>O1CCCC1>[CH2:1]([C:8]1[C:9]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:10]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:11]2[N:12]([C:14]([Cl:29])=[CH:15][CH:16]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of ethyl 2-benzyl-4-(4-fluorophenyl)pyrrolo[1,2-b]pyridazine-3-carboxylate (730 mg) in tetrahydrofuran (10 ml) was added N-chlorosuccinimide (260 mg) and the mixture was stirred at 20° C. for 2 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with aqueous sodium thiosulfate, water and brine, dried over magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography eluting with a mixture of toluene and ethyl acetate (10:1) to give ethyl 2-benzyl-7-chloro-4-(4-fluorophenyl)pyrrolo[1,2-b]pyridazine-3-carboxylate (285 mg) as an yellow oil.

Workup

customThe mixture was partitioned between ethyl acetate and water
customThe organic layer was separated
washwashed with aqueous sodium thiosulfate, water and brine
dry with materialdried over magnesium sulfate
customevaporated
customThe residue was purified by silica gel column chromatography
washeluting with a mixture of toluene and ethyl acetate (10:1)

Sources & evidence

ORD record: ord-9c97d6d92c3a48f2b02d11a4538d4756
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07317009B2

Reaction notes

Loading…