3-Fluorosulfonyl-6-methoxypyridazine → 3-Methoxy-6-(5-fluoro-3-methyl-benzofuran-2-sulfonyl)-pyridazine

HRID 1369470

Reaction equation

C([Li])CCC.[F:6][C:7]1[CH:8]=[CH:9][C:10]2[O:14][CH:13]=[C:12]([CH3:15])[C:11]=2[CH:16]=1.F[S:18]([C:21]1[N:22]=[N:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)(=[O:20])=[O:19]>C1COCC1>[CH3:28][O:27][C:24]1[N:23]=[N:22][C:21]([S:18]([C:13]2[O:14][C:10]3[CH:9]=[CH:8][C:7]([F:6])=[CH:16][C:11]=3[C:12]=2[CH3:15])(=[O:20])=[O:19])=[CH:26][CH:25]=1

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyl lithium (2.5 M in hexane, 11 mmol, 4.83 mL) was added dropwise over 15 minutes to a solution of 5-fluoro-3-methyl benzofuran (11 mmol, 1.65 mg) in THF (20 mL) cooled to −78° C. To this was added 3-fluorosulfonyl-6-methoxy-pyridazine (11 mmol, 2.11 g) and stirred for 30 minutes. The reaction mixture was allowed to come to room temperature overnight and was then quenched with EtOAc (40 mL) and H2O (10 mL). The organic portion was collected, dried, filtered and the filtrate was evaporated to dryness to obtain a crude product, which was purified by silica gel chromatography (eluent: hexanes:EtOAc::4:1) to obtain the desired product: 3-methoxy-6-(5-fluoro-3-methyl-benzofuran-2-sulfonyl)-pyridazine (22%, 781 mg).

Workup

waitto come to room temperature overnight
customwas then quenched with EtOAc (40 mL) and H2O (10 mL)
customThe organic portion was collected
customdried
filtrationfiltered
customthe filtrate was evaporated to dryness
customto obtain a crude product, which
customwas purified by silica gel chromatography (eluent: hexanes:EtOAc::4:1)

Sources & evidence

ORD record: ord-8fb61c798717489fb552626f78472542
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06579879B2

Linked notes

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