Potassium Phosphate, Tribasic → US10023592, Example 381

HRID 518544Notizen

Reaktionsgleichung

Br[C:2]1[C:3]([O:14][CH2:15][CH:16]2[CH2:18][CH2:17]2)=[CH:4][C:5](=[O:13])[N:6]([CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:7]=1.[CH3:19][N:20]1[CH:25]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:23]=[CH:22][C:21]1=[O:35].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:16]1([CH2:15][O:14][C:3]2[C:2]([C:24]3[CH:23]=[CH:22][C:21](=[O:35])[N:20]([CH3:19])[CH:25]=3)=[CH:7][N:6]([CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:5](=[O:13])[CH:4]=2)[CH2:18][CH2:17]1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

The title compound from step 4 (50 mg, 0.15 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (42 mg, 0.18 mmol), Pd(dppf)Cl2 (11 mg, 14.9 umol) and K3PO4 (63 mg, 0.3 mmol) in dioxane (5 mL) and water (5 drops) were degassed and then heated to 70° C. under N2 overnight. The reaction mixture was then concentrated under reduced pressure. The residue was purified by column chromatography (PE:DCM:EA=3:0:1 to 0:1:4) followed by preparative HPLC to afford the title compound (17.09 mg, 31.5%) as an off-white solid. 1H NMR (CDCl3, 400 MHz) δ 7.50 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 7.43 (d, J=2.4 Hz, 1H), 6.71 (d, J=9.2 Hz, 1H), 5.96 (s, 1H), 5.16 (s, 2H), 3.86 (d, J=6.8 Hz, 1H), 3.63 (s, 3H), 2.99 (s, 3H), 1.26-1.21 (m, 1H), 0.70-0.66 (m, 2H), 0.36-0.32 (m, 2H). LCMS: 365.0 (M+1)+

Aufarbeitung

concentrationThe reaction mixture was then concentrated under reduced pressure
customThe residue was purified by column chromatography (PE:DCM:EA=3:0:1 to 0:1:4)

Quellen und Nachweise

ORD-Eintrag: ord-8af9d14cfcc14859a5672655846e4390
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09115114B2

Notizen zur Reaktion

Wird geladen…