Potassium Carbonate → 2-[(3-methyl-3,4-dihydro-2H-chromen-5-yl)oxy]-5-nitropyridine

HRID 527589Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=1.[CH3:17][CH:18]1[CH2:27][C:26]2[C:25]([OH:28])=[CH:24][CH:23]=[CH:22][C:21]=2[O:20][CH2:19]1>CN(C)C=O>[CH3:17][CH:18]1[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[O:28][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=2)[O:20][CH2:19]1

Participants

Conditions

Temperature: 110 °C

Procedure

In a microwave vial, 3-methyl-3,4-dihydro-2H-chromen-5-ol (Intermediate 117, 53 mg), potassium carbonate (134 mg, 0.968 mmol) and 2-chloro-5-nitropyridine (51.2 mg, 0.323 mmol) were dissolved in N,N-dimethylformamide (2 ml) to give a light brown solution. The reaction vessel was sealed and heated in Biotage Initiator at 110° C. for 1 hour. After cooling, the reaction mixture was quenched with 5 ml of water and diluted with 10 ml of Et2O. Phases were separated by a separating funnel. The aqueous phase was extracted with 3×10 ml of Et2O. The collected organic phase were dried using a hydrophobic frit and evaporated under vacuum to give the title compound as a brown oil (181 mg).

Workup

customto give a light brown solution
customThe reaction vessel was sealed
temperatureAfter cooling
customthe reaction mixture was quenched with 5 ml of water
additiondiluted with 10 ml of Et2O
customPhases were separated by a separating funnel
extractionThe aqueous phase was extracted with 3×10 ml of Et2O
customThe collected organic phase were dried
customevaporated under vacuum

Sources & evidence

ORD record: ord-74d0bae01a2442918b498614305f842d
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346790B2

Reaction notes

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