Potassium Carbonate → 2-[(3-Methyl-1,3-dihydro-2-benzofuran-4-yl)oxy]-5-nitropyridine

HRID 527576Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][CH:18]1[C:22]2[C:23]([OH:27])=[CH:24][CH:25]=[CH:26][C:21]=2[CH2:20][O:19]1>CN(C)C=O>[CH3:17][CH:18]1[C:22]2[C:23]([O:27][C:2]3[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=3)=[CH:24][CH:25]=[CH:26][C:21]=2[CH2:20][O:19]1

Participants

Conditions

Temperature: 110 °C

Procedure

In a microwave vial 3-methyl-1,3-dihydro-2-benzofuran-4-ol (Intermediate 98, 24 mg) was dissolved in N,N-dimethylformamide (1.5 ml) to give a pale yellow solution. 2-chloro-5-nitropyridine (24.07 mg, 0.152 mmol) and potassium carbonate (62.9 mg, 0.455 mmol) were added. The reaction vessel was sealed and heated in a microwave Biotage Initiator at 110° C. for 1 hour. After cooling, the reaction mixture was quenched with 5 ml of water and diluted with 25 ml of Et2O. The organic phase was washed with water (3×10 mL) and the phases were separated. The organic phase was passed through a phase separator cartridge and evaporated under vacuum to give the title compound (38.3 mg).

Workup

customto give a pale yellow solution
customThe reaction vessel was sealed
temperatureAfter cooling
customthe reaction mixture was quenched with 5 ml of water
additiondiluted with 25 ml of Et2O
washThe organic phase was washed with water (3×10 mL)
customthe phases were separated
customevaporated under vacuum

Sources & evidence

ORD record: ord-d12719b541eb4e4b9fca4e98fed12218
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346790B2

Reaction notes

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