Hydrochloric Acid → HCID 117600653, compound
Reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[Br:17][C:18]1[CH:19]=[C:20]([C:28]([C:30]2[O:31][C:32]([CH3:35])=[N:33][N:34]=2)=O)[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1.Cl>C1COCC1.O>[CH2:15]([O:14][C:12](=[O:13])/[CH:11]=[C:28](/[C:20]1[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=[C:18]([Br:17])[CH:19]=1)\[C:30]1[O:31][C:32]([CH3:35])=[N:33][N:34]=1)[CH3:16]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a suspension of NaH (60%, 1.13 g, 28.35 mmol) in dry THF (20 mL) was added ethyl 2-(diethoxyphosphoryl)acetate (6.49 g, 28.35 mmol) at −78° C. After being stirred at −78° C. for 1 hour, a solution of (3-Bromo-5-trifluoromethyl-phenyl)-(5-methyl-[1,3,4]oxadiazol-2-yl)-methanone (9.047 g, 27 mmol) in 20 ml THF was added drop wise over 30 min. The mixture was stirred at −78° C. for 30 min and then warmed to room temperature followed by stirring overnight. The mixture was cooled to 0° C. and treated with water (50 mL), pH value was adjusted to 6 with HCl (0.5N) and extracted with EtOAc (50 mL×3). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with a petroleum ether/EtOAc mixture to afford 9 g of the desired product (Yield: 90%).
Workup
- stirringThe mixture was stirred at −78° C. for 30 min
- temperaturewarmed to room temperature
- stirringby stirring overnight
- temperatureThe mixture was cooled to 0° C.
- extractionextracted with EtOAc (50 mL×3)
- dry with materialThe combined organic layers were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel chromatography
- washeluting with a petroleum ether/EtOAc mixture
Sources & evidence
- ORD record
- ord-27c0bf5ea45748babe0a5fab2952ad9f
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150526B2
Reaction notes
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