Dimethylformamide → Isopropyl 5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxa-diazol-3-yl)benzoate

HRID 2075955Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([O:24][CH3:25])=[CH:11][C:12]([C:18]2[N:22]=[C:21]([CH3:23])[O:20][N:19]=2)=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH:27]([CH3:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.O>[CH2:1]([O:8][C:9]1[C:10]([O:24][CH3:25])=[CH:11][C:12]([C:18]2[N:22]=[C:21]([CH3:23])[O:20][N:19]=2)=[C:13]([CH:17]=1)[C:14]([O:16][CH:27]([CH3:29])[CH3:28])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzoic acid (reference example 5-1) (308 mg), 2-iodopropane (0.225 mL), potassium carbonate (312 mg) and N,N-dimethylformamide (2.6 mL) was stirred at 60° C. for 2.5 hours. After cooling to room temperature, water and ethyl acetate were added to the mixture. The separated organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (342 mg).

Workup

temperatureAfter cooling to room temperature
washThe separated organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-43411c080f584cd5917a9bbdb9161955
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923462B2

Reaction notes

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