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

HRID 1047290Notes

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 the 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-12b6614986da423ab980d9d4228d8c62
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569494B2

Reaction notes

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