Sodium Bicarbonate → 5-[4-(4-Pyridinyl)-6-quinolinyl]-3-pyridinesulfonamide

HRID 472066Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](B4OC(C)(C)C(C)(C)O4)[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.Br[C:27]1[CH:28]=[C:29]([S:33]([NH2:36])(=[O:35])=[O:34])[CH:30]=[N:31][CH:32]=1.C([O-])(O)=O.[Na+]>O1CCOCC1>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:27]4[CH:28]=[C:29]([S:33]([NH2:36])(=[O:35])=[O:34])[CH:30]=[N:31][CH:32]=4)[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-(4-pyridinyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (250 mg, 0.75 mmol), 5-bromopyridine-3-sulfonamide (213 mg, 0.9 mmol), tetrakistriphenylphosphine palladium (0) (95 mg, 0.08 mmol), and saturated aqueous NaHCO3 (2.5 mL), and dioxane (5 mL)) was heated at 120° C. for 1 h and cooled to room temperature. The reaction mixture was filtered through Celite and the solvent was removed under reduced pressure. The crude product was purified by Gilson reverse phase HPLC (8-25% 6 min gradient 0.1% TFA in H2O/CH3CN) followed by neutralization with saturated aqueous NaHCO3 and extracted into EtOAc. Evaporation provided the title compound as an off white solid. (85 mg, 31%). ESMS [M+H]+=363.1

Workup

temperaturecooled to room temperature
filtrationThe reaction mixture was filtered through Celite
customthe solvent was removed under reduced pressure
customThe crude product was purified by Gilson reverse phase HPLC (8-25% 6 min gradient 0.1% TFA in H2O/CH3CN)
extractionextracted into EtOAc
customEvaporation

Sources & evidence

ORD record: ord-c81166692e2f4f5689e74daf9f19cba1
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633187B2

Reaction notes

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