Sodium ethoxide → 2-(3-Bromo-4-(trifluoromethyl)phenyl)-6-ethoxyimidazo[1,2-b]pyridazine

HRID 539765Notes

Reaction equation

[CH3:1][CH2:2][O-:3].[Na+].[Br:5][C:6]1[CH:7]=[C:8]([C:16]2[N:17]=[C:18]3[N:23]([CH:24]=2)[N:22]=[C:21](Cl)[CH:20]=[CH:19]3)[CH:9]=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13]>C1COCC1>[Br:5][C:6]1[CH:7]=[C:8]([C:16]2[N:17]=[C:18]3[CH:19]=[CH:20][C:21]([O:3][CH2:2][CH3:1])=[N:22][N:23]3[CH:24]=2)[CH:9]=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13]

Participants

Conditions

Temperature: 50 °C

Procedure

NaOEt (21% in EtOH, 2.97 mL) is added to a mixture of 2-[3-bromo-4-(trifluoromethyl)phenyl]-6-chloro-imidazo[2,1-f]pyridazine (1.5 g, 3.98 mmol) in THF (50 mL). The mixture is stirred for 4 hours at 50° C., then the THF solution is concentrated onto celite and purified by silica gel chromatography (0-100% EtOAc in Hexanes) to give the title compound (1.36 g, 88.8% yield). LCMS (m/z)=386.3, 388.3 [M+H]+, tR=3.34 min. (compound same as Example 204)

Workup

concentrationthe THF solution is concentrated onto celite
custompurified by silica gel chromatography (0-100% EtOAc in Hexanes)

Sources & evidence

ORD record: ord-6511ef0dd9ff4988bb3273eca10972bf
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871767B2

Reaction notes

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