4-Nitroaniline → 6-chloro-N-(4-nitrophenyl)imidazo[1,2-b]pyridazin-8-amine

HRID 2239851Notes

Reaction equation

Cl.Br[C:3]1[C:4]2[N:5]([CH:10]=[CH:11][N:12]=2)[N:6]=[C:7]([Cl:9])[CH:8]=1.[N+:13]([C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1)([O-:15])=[O:14].CC(C)([O-])C.[K+].C1COCC1>CN(C=O)C>[Cl:9][C:7]1[CH:8]=[C:3]([NH:20][C:19]2[CH:21]=[CH:22][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=2)[C:4]2[N:5]([CH:10]=[CH:11][N:12]=2)[N:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

In a 2 dram reaction vial was added 8-bromo-6-chloroimidazo[1,2-b]pyridazine hydrochloric acid salt (0.5 g, 1.9 mmol) from Example I(1), step 1b, 4-nitroaniline (0.27 g, 1.9 mmol), 1.0 M potassium tert-butoxide in THF (7.6 ml, 7.6 mmol) and DMF (1.4 ml). Under N2, the reaction was stirred for 16 hr at 50° C. and the concentrated in vacuo. The resulting material was taken up in ethyl acetate and washed with H2O (2×50 ml) and then brine (1×20 ml). the organic layers were combined and dried over Na2SO4 and filtered. Following solvent evaporation, 0.42 g of crude 6-chloro-N-(4-nitrophenyl)imidazo[1,2-b]pyridazin-8-amine was obtained.

Workup

customIn a 2 dram reaction
concentrationthe concentrated in vacuo
washwashed with H2O (2×50 ml)
dry with materialdried over Na2SO4
filtrationfiltered
customFollowing solvent evaporation

Sources & evidence

ORD record: ord-c5107f68ef3a49af9fa072c258bfbfb1
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723336B2

Reaction notes

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