Cesium carbonate → methyl 3-[2-(2,4-difluorophenoxy)-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl]-4-methoxybenzoate

HRID 1454957Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][C:10](=[O:24])[C:11]=2[C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=2[O:22][CH3:23])[C:15]([O:17][CH3:18])=[O:16])[N:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[F:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=1[OH:39]>CN1C(=O)CCC1>[F:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=1[O:39][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][C:10](=[O:24])[C:11]=2[C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=2[O:22][CH3:23])[C:15]([O:17][CH3:18])=[O:16])[N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 3-(2-chloro-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl)-4-methoxybenzoate (1.05 g, 3.05 mmol) and Cs2CO3 (2.97 g, 9.15 mmol) dissolved in NMP (20 mL) was added 2,4 difluoro phenol (475 mg, 3.66 mmol). The mixture was heated to 80° C. for 1 hr until the reaction was complete via LCMS analysis. The reaction was poured into 500 mL of ice/H2O and the solid precipitate was collected. The crude residue was purified via silica gel chromatography (EtOAc/CH2Cl2, MeOH) to yield the title compound.

Workup

customthe solid precipitate was collected
customThe crude residue was purified via silica gel chromatography (EtOAc/CH2Cl2, MeOH)

Sources & evidence

ORD record: ord-0ce05da8e0d7418d92f6486c5635e4d1
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482345B2

Reaction notes

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