Potassium Fluoride → 4-(3-Bromoimidazo[1,2-b]pyridazin-6-yl)-3-(3-fluorophenyl)morpholine

HRID 1890672Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][O:12][CH2:11][CH2:10][NH:9]2)[CH:5]=[CH:6][CH:7]=1.[Br:14][C:15]1[N:19]2[N:20]=[C:21](Cl)[CH:22]=[CH:23][C:18]2=[N:17][CH:16]=1.[F-].[K+]>CS(C)=O>[Br:14][C:15]1[N:19]2[N:20]=[C:21]([N:9]3[CH2:10][CH2:11][O:12][CH2:13][CH:8]3[C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)[CH:22]=[CH:23][C:18]2=[N:17][CH:16]=1

Participants

Conditions

Temperature: 180 °C

Procedure

In step 2-5, a suspension of 3-(3-fluorophenyl)morpholine (1.59 g, 6.9 mmol), 3-bromo-6-chloroimidazo[1,2-b]pyridazine (12-1) (1.5 g, 8.29 mmol) and potassium fluoride (1.6 g, 27.6 mmol) in DMSO (6 mL) was heated at 180° C. for 18 hours while stirring. The resulting solution was cooled to room temperature and purified with HPLC to yield 4-(3-Bromoimidazo[1,2-b]pyridazin-6-yl)-3-(3-fluorophenyl)morpholine (2-5) as a yellow foam.

Workup

temperatureThe resulting solution was cooled to room temperature
custompurified with HPLC

Sources & evidence

ORD record: ord-74fc6dfe4647454cb5e896e1b9afd4b5
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507488B2

Reaction notes

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