Potassium Carbonate → 6-Bromo-4-(4-pyridinyl)quinoline

HRID 472065Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2I.[N:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[C:16]1[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A 1 L sealed tube charged with 6-bromo-4-iodoquinoline (11.58 g, 0.0347 mol), 4-pyridineboronic acid (5.97 g, 0.0486 mol), tetrakis(triphenyphosphine)palladium[0] (2.0 g, 0.00173 mol), 2 M aqueous potassium carbonate (152 mL) and 1,4-dioxane (152 mL) was stirred at 100° C. for 28 hrs. After cooling to rt, the organic layer was separated and the aqueous portion extracted with EtOAc (200 mL×3). The combined organic extracts were dried (Na2SO4), filtered and partially concentrated in vacuo. The resultant mixture was filtered to give the title compound (9.13 g) as a tan solid. The residual supernatant was concentrated to dryness and purified by silica gel chromatography (100% ethyl acetate to 2% methanol in ethyl acetate) to provide an additional 0.036 g of the title compound as a tan solid (combined 9.166 g, 92% yield).

Workup

customA 1 L sealed tube
temperatureAfter cooling to rt
customthe organic layer was separated
extractionthe aqueous portion extracted with EtOAc (200 mL×3)
dry with materialThe combined organic extracts were dried (Na2SO4)
filtrationfiltered
concentrationpartially concentrated in vacuo
filtrationThe resultant mixture was filtered

Sources & evidence

ORD record: ord-5cd1d37898604da79eb255a211737f1e
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633187B2

Reaction notes

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