3,4-dihydro-2H-pyran → HCID 58298306, compound

HRID 717192Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[CH:11][NH:10][N:9]=2)=[C:4]([F:13])[C:3]=1[CH3:14].[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1>O1CCCC1.C(OCC)(=O)C.CS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][O:15]3)[CH:11]=[N:10][N:9]=2)=[C:4]([F:13])[C:3]=1[CH3:14]

Participants

Conditions

Temperature: 85 °C

Procedure

Methanesulfonic acid (0.090 mL, 1.390 mmol) was added to a stirred solution of 3-(4-bromo-2-fluoro-3-methylphenyl)-1H-1,2,4-triazole (7.0 g, 27.3 mmol) and 3,4-dihydro-2H-pyran (12.68 mL, 139 mmol) in tetrahydrofuran (33 mL). The resulting mixture stirred at 85° C. under a reflux condenser under nitrogen for 20 h. The mixture was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified using flash chromatography (20-30-50% ethyl acetate in hexane). Product containing fractions were combined and solvent removed under reduced pressure to afford desired product (8.8 g, 95% yield) as a yellow solid. MS (ESI) m/z 340.0 [M]+

Workup

washwashed with saturated aqueous sodium bicarbonate and brine
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified
additionProduct containing fractions
customsolvent removed under reduced pressure

Sources & evidence

ORD record: ord-4dd2c6bd9b724ea2ab57e03959e63e61
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193692B2

Reaction notes

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