Tetrahydrofuran → HCID 86673687, compound

HRID 244385Notes

Reaction equation

Cl[C:2]1[N:3]=[N:4][C:5]([CH3:25])=[C:6]([C:17]2[CH:22]=[CH:21][C:20]([C:23]#[CH:24])=[CH:19][CH:18]=2)[C:7]=1[C:8]1[C:13]([F:14])=[CH:12][C:11](F)=[CH:10][C:9]=1[F:16].[CH3:26][O-:27].[Na+].[O:29]1[CH2:33]CCC1>O>[F:16][C:9]1[CH:10]=[C:11]([O:27][CH3:26])[CH:12]=[C:13]([F:14])[C:8]=1[C:7]1[C:6]([C:17]2[CH:22]=[CH:21][C:20]([C:23]#[CH:24])=[CH:19][CH:18]=2)=[C:5]([CH3:25])[N:4]=[N:3][C:2]=1[O:29][CH3:33]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 3-chloro-5-(4-ethynylphenyl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine (Compound No. 2, 1.0 g), sodium methoxide (30% solution in methanol, 1.78 g) and 20 ml of tetrahydrofuran is heated to 55° C. for 2 h. Subsequently the reaction mixture is cooled, diluted with water and extracted with ethyl acetate. The combined organic layer is washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure. The residue is purified by chromatography on silica gel, using a mixture of heptane/ethyl acetate 2:1 as eluent to obtain 4-(2,6-difluoro-4-methoxyphenyl)-5-(4-ethynylphenyl)-3-methoxy-6-methylpyridazine (Compound No. 4) as colourless crystals, m.p. 192-193° C.

Workup

temperatureSubsequently the reaction mixture is cooled
extractionextracted with ethyl acetate
washThe combined organic layer is washed with water and brine
dry with materialdried over sodium sulfate
customevaporated under reduced pressure
customThe residue is purified by chromatography on silica gel
additiona mixture of heptane/ethyl acetate 2:1 as eluent

Sources & evidence

ORD record: ord-4f40ea59e86d43fdaa4b1b8acc2a20b8
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658644B2

Reaction notes

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