Ethyl Acetate → HCID 69007483, compound

HRID 1376110Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]#[N:13])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1.CC(C)([O-])C.[K+].[C:20]([O:23][CH2:24][CH2:25]Br)(=[O:22])[CH3:21].C(OCC)(=O)C>C1COCC1>[CH2:24]([O:23][C:20]([C:21]1[N:8]([C:9](=[O:11])[CH3:10])[C:6]2[C:5]([C:12]=1[NH2:13])=[CH:4][CH:3]=[C:2]([Cl:1])[CH:7]=2)=[O:22])[CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

Stir and cool to 0° C. a mixture of N-(5-chloro-2-cyanophenyl)acetamide (see Example 8, 1.0 g, 5.14 mmol) and THF (10 mL) and add potassium tert-butoxide (6.2 mL, of a 1M solution in THF) and stir at 0° C. for 30 min. Add bromoethyl acetate (0.6 mL) in one portion. Stir at room temperature for 2 h. Quench the reaction with water (40 mL) and stir with ethyl acetate. Separate the layers and reextract the aqueous with ethyl acetate. Combine the organic extracts and wash with water and brine. Dry over MgSO4 and concentrate under reduced pressure to obtain a brown solid. Triturate the solid with ether and collect a beige solid. Chromatograph the solid on silica gel with 2% ethyl acetate/dichloromethane followed by 10% ethyl acetate/dichloromethane to obtain 0.65 g (45%) of the title compound as a beige solid: MS 281(M+H), HPLC: Rt=3.20 min., TLC (silica gel, 10% ethyl acetate/dichloromethane) Rf=0.53.

Workup

stirringStir at room temperature for 2 h
customQuench
customthe reaction with water (40 mL)
customSeparate the layers
washwash with water and brine
dry with materialDry over MgSO4
concentrationconcentrate under reduced pressure
customto obtain a brown solid
customTriturate the solid with ether
customcollect a beige solid

Sources & evidence

ORD record: ord-7c24a12b06f04439ab928568a7caaeea
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07169925B2

Reaction notes

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