Potassium Carbonate → HCID 86699303, compound

HRID 516981Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[C:13]([CH3:14])=[CH:12][C:11]([OH:15])=[CH:10][C:9]2=[O:16])[C:5]([CH3:17])=[CH:4][N:3]=1.[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.CCCCCCC>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH2:24][C:23]3[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=3)=[CH:10][C:9]2=[O:16])[C:5]([CH3:17])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2′-chloro-4-hydroxy-6,5′-dimethyl-[1,4′]bipyridinyl-2-one of part A (6.0 g, 20.1 mmol) in N,N-dimethylformamide (20 mL) was added 4-methoxybenzylchloride (2.73 mL, 20.1 mmol), potassium carbonate (6.93 g, 50.2 mmol) and 18-crown-6 (100 mg). The slurry was heated at 60° C. for 3 h and was stirred at ambient temperature for 18 h. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The solution was concentrated in vacuo to provide a brown oil. Normal phase chromatography (ethyl acetate/heptane) provided the alkylated product as a light yellow solid (4.6 g): MS (ES) m/e 371 (M+H).

Workup

customThe reaction mixture was partitioned between ethyl acetate and water
washThe organic layer was washed with water and brine
dry with materialdried over magnesium sulfate
concentrationThe solution was concentrated in vacuo
customto provide a brown oil

Sources & evidence

ORD record: ord-1826ac3eda9b4d7e91fc06f460fa999f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115089B2

Reaction notes

Loading…