Potassium Carbonate → 3-Ethyl-4-[(5-nitro-2-pyridinyl)oxy]-1,2-benzisoxazole

HRID 527527Notes

Reaction equation

[CH2:1]([C:3]1[C:7]2=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=[C:6]2[O:5][N:4]=1)[CH3:2].C(C1OC2C(=C(O)C=CC=2)N=1)C.Cl[C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][N:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([C:3]1[C:7]2[C:8]([O:12][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][N:27]=3)=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][N:4]=1)[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 3-ethyl-1,2-benzisoxazol-4-ol and 2-ethyl-1,3-benzoxazol-4-ol (Intermediate 31, 38 mg), was dissolved in DMF (3.0 mL) and 2-chloro-5-nitropyridine (36.9 mg, 0.23 mmol) was added, followed by potassium carbonate (97 mg, 0.70 mmol). The reaction mixture was heated under microwave irradiation at 110° C. for 1 hour. After removal of the volatiles, the crude was charged on a silica gel column and eluted with Cyclohexane/EtOAc (from 1/0 to 1/1) to afford the title compound (9.5 mg).

Workup

customAfter removal of the volatiles
additionthe crude was charged on a silica gel column
washeluted with Cyclohexane/EtOAc (from 1/0 to 1/1)

Sources & evidence

ORD record: ord-4f549309211446ad846ab73123da2262
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346790B2

Reaction notes

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