4-(Methylthio)phenylboronic acid → HCID 21934136, compound

HRID 891278Notes

Reaction equation

HRID 891278 reaction equation
[C:1]1([N:7]2[C:12](=[O:13])[C:11]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[C:10](OS(C(F)(F)F)(=O)=O)[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:29][S:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1>>[C:1]1([N:7]2[C:12](=[O:13])[C:11]([C:14]3[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=3)=[C:10]([C:34]3[CH:35]=[CH:36][C:31]([S:30][CH3:29])=[CH:32][CH:33]=3)[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 27339594-(Methylthio)phenylboronic acidHCID 10158698HCID 10158698, compound

Product 1

HCID 21934136HCID 21934136, compoundYield 92%

Procedure

The 2-phenyl-4-(4-fluorophenyl)-5-trifluoromethanesulfonyloxy-3(2H)-pyridazinone was coupled with 4-(methylthio)phenylboronic acid as in Example 9 to provide 2-phenyl-4-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-3(2H)-pyridazinone (yield: 915 mg, 92%) which was immediately oxidized with peracetic acid as in Example 9 to provide the title compound after column chromatography (silica gel, 1:1 hexanes-ethyl acetate) and crystallization from diethyl ether-hexanes (yield: 288 mg, 69%). mp 219-220° C. 1H NMR (300 MHz, DMSO-d6) δ 3.25 (s, 3H), 7.15 (t, J=9 Hz, 2H), 7.30 (m, 2H), 7.46 (m, 1H), 7.56 (m, 4H), 7.64 (m, 2H), 7.90 (d, J=9 Hz, 2H), 8.24 (s, 1H). MS (DCI/NH3) m/z 421 (M+H)+, 438 (M+NH4)+.

Sources & evidence

ORD record
ord-bdde26e66cf140d8bafa8041955fd7a8
Source dataset
uspto-grants-2006_02
Patent number
US07001895B2

Reaction notes

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