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

HRID 527581Notes

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+].[CH2:17]([CH:19]1[C:23]2[C:24]([OH:28])=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:21][O:20]1)[CH3:18]>CN(C)C=O>[CH2:17]([CH:19]1[C:23]2[C:24]([O:28][C:2]3[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=3)=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:21][O:20]1)[CH3:18]

Participants

Conditions

Temperature: 110 °C

Procedure

In a 0.5-2.0 ml micro-wave vial 3-ethyl-1,3-dihydro-2-benzofuran-4-ol (Intermediate 106, 49.7 mg) was dissolved in N,N-dimethylformamide (1.5 ml) to give a pale yellow solution. 2-chloro-5-nitropyridine (48.0 mg, 0.303 mmol) and potassium carbonate (125 mg, 0.908 mmol) were added. The reaction vessel was sealed and heated in micro-wave Biotage Initiator at 110° C. for 1 hour. After cooling, the reaction completed. The reaction mixture was then quenched with 5 ml of water and diluted with 25 ml of Et2O. The aqueous phase was extracted with 3×10 ml of Et2O. The collected organic phases were passed through a phase separator cartridge and evaporated under vacuum to give the title compound as a pale yellow oil (97.6 mg).

Workup

customto give a pale yellow solution
customThe reaction vessel was sealed
temperatureAfter cooling
customThe reaction mixture was then quenched with 5 ml of water
additiondiluted with 25 ml of Et2O
extractionThe aqueous phase was extracted with 3×10 ml of Et2O
customevaporated under vacuum

Sources & evidence

ORD record: ord-260478dee2c348d2a8120e6f93059796
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346790B2

Reaction notes

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