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

HRID 2239817Notes

Reaction equation

Br[C:2]1[C:3]2[N:4]([CH:9]=[CH:10][N:11]=2)[N:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=1.CC([O-])(C)C.[K+]>C1COCC1>[Cl:8][C:6]1[CH:7]=[C:2]([NH:21][C:18]2[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH3:12])=[CH:20][CH:19]=2)[C:3]2[N:4]([CH:9]=[CH:10][N:11]=2)[N:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

(1c variation 1) To a mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (257 mg, 0.956 mmol) from 1b in THF (2.0 ml) was added p-phenetidine (131 mg, 0.956 mmol) and a 1.0 M solution of KOt-Bu in THF (2.5 eq, 2.4 ml, 2.39 mmol). The mixture was allowed to heat at 50° C. for 1 hour. The solution was then concentrated in vacuo to provide crude 6-chloro-N-(4-ethoxyphenyl)imidazo[1,2-b]pyridazin-8-amine as a solid. The solid was then used as is in the following step.

Workup

concentrationThe solution was then concentrated in vacuo

Sources & evidence

ORD record: ord-3e3031e93fad490fa0eb1801f52a4f3e
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723336B2

Reaction notes

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