Trimethylsilyldiazomethane → HCID 58072511, compound

HRID 1624850Notes

Reaction equation

[OH:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:6]=[C:5]([C:18]2[N:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:21]=[CH:20][CH:19]=2)[C:4](=[O:29])[CH:3]=1.[CH3:30][Si](C=[N+]=[N-])(C)C>CO>[CH3:30][O:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:17])[F:16])[CH:9]=2)[N:6]=[C:5]([C:18]2[N:22]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:21]=[CH:20][CH:19]=2)[C:4](=[O:29])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution 6-hydroxy-3-(1-phenyl-1H-pyrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (0.23 g, 0.58 mmol) in MeOH (10 mL) was added dropwise trimethylsilyldiazomethane (2 M solution in diethylether, 8.0 mL, 16.0 mmol) at 0° C., and the mixture was stirred at 0° C. for 1 h. The mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with AcOEt/hexane (20/80-100/0) and recrystallized from AcOEt/hexane to give the title compound (0.023 g, 10% yield) as white crystals: mp 139-141° C.; NMR (300 MHz, CDCl3): δ ppm 3.90 (3H, s), 6.14 (1H, s), 6.97-7.02 (1H, m), 7.13 (1H, s), 7.22 (1H, d, J=1.9 Hz), 7.31-7.44 (6H, m), 7.56-7.61 (1H, m), 7.76 (1H, d, J=1.9 Hz). LC-MS (ESI) m/z 413 [M+H]+. Anal. Calcd for C21H15F3N4O2: C, 61.17; H, 3.67; N, 13.59.

Workup

concentrationThe mixture was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography
washeluting with AcOEt/hexane (20/80-100/0)
customrecrystallized from AcOEt/hexane

Sources & evidence

ORD record: ord-01d390ee216148a38d520302ae49607b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778944B2

Reaction notes

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