Sodium Bicarbonate → HCID 73057757, compound

HRID 2207333Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:18])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[CH:13][CH:12]=3)=[CH:4][CH:3]=1.[CH3:19][N:20]1[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=[N:21]1.C(=O)([O-])O.[Na+]>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:19][N:20]1[CH:24]=[C:23]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[NH:9][C:10](=[O:18])[C:11]4[C:16]([CH:17]=3)=[CH:15][N:14]=[CH:13][CH:12]=4)=[CH:4][CH:3]=2)[CH:22]=[N:21]1

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of 3-(4-bromo-phenyl)-2H-[2,6]naphthyridin-1-one (55.0 mg, 0.18 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (57 mg, 0.27 mmol) and sodium hydrogen carbonate (18.4 mg, 0.22 mmol) in DMF (0.5 ml) and water (0.25 ml) is flushed with nitrogen and heated to 40° C. Then bis(triphenylphosphine)-palladium(II)-chloride (2.6 mg, 0.004 mmol) is added. The reaction mixture is heated to 80° C. and stirred at this temperature for 20 hours. The mixture is allowed to cool to room temperature and excess water is added. The resulting precipitate is filtered off washed with water and 2-propanol and dried under vacuum to afford 3-[4-(1-methyl-1H-pyrazol-4-yl)-phenyl]-2H-[2,6]naphthyridin-1-one as grey solid; HPLC/MS 1.47 min (A), [M+H] 303;

Workup

customis flushed with nitrogen
temperatureThe reaction mixture is heated to 80° C.
temperatureto cool to room temperature
filtrationThe resulting precipitate is filtered off
washwashed with water and 2-propanol
customdried under vacuum

Sources & evidence

ORD record: ord-a931236877964004abfd85dd2d42e99e
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376433B2

Reaction notes

Loading…