Potassium Carbonate → HCID 66731903, compound

HRID 1963208Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].CC1(C)C(C)(C)OB([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[C:28]([CH3:36])[CH:27]=2)O1>CO.Cl[Pd]Cl>[CH3:36][C:28]1[CH:27]=[C:26]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH:31]=[CH:30][C:29]=1[C:32]([F:33])([F:34])[F:35]

Participants

Conditions

Temperature: 100 °C

Procedure

Methyl 2-chloroisonicotinate (0.996 g, 5.80 mmol), potassium carbonate (1.042 g, 7.54 mmol), 4,4,5,5-tetramethyl-2-(3-methyl-4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (1.66 g, 5.80 mmol) and PdCl2 (dppf) (0.105 g, 0.15 mmol) were mixed in methanol (20 mL) in two microwave vials. The vials were capped and heated at 100° C. for 10 min in a single node microwave reactor. The solution was partitioned between water and ethyl acetate. The organic layer was isolated, dried over Na2SO4, filtered through celite and the solvent was evaporated. Automated column chromatography using the Biotage equipment. Gradient eluation using heptane-ethyl acetate, 0% to 50%. Methyl 2-(3-methyl-4-(trifluoromethyl)phenyl)-isonicotinate (1.22 g, 71%) was isolated. 1H NMR (600 MHz, cdcl3) δ 2.57 (s, 3H), 3.99 (s, 3H), 7.70 (d, 1H), 7.81 (dd, 1H), 7.91 (d, 1H), 7.98 (s, 1H), 8.29 (s, 1H), 8.84 (d, 1H).

Workup

customThe vials were capped
customThe solution was partitioned between water and ethyl acetate
customThe organic layer was isolated
dry with materialdried over Na2SO4
filtrationfiltered through celite
customthe solvent was evaporated

Sources & evidence

ORD record: ord-d3edd3acfd9648d69bc424c238da0a4e
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415378B2

Reaction notes

Loading…