Potassium Phosphate, Tribasic → 12-(3,4-Dimethoxyphenyl)-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one

HRID 926112

Reaktionsgleichung

Br[C:2]1[CH:11]=[N:10][C:9]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:7](=[O:21])[N:6]3[N:22]=[CH:23][N:24]=[C:5]3[C:4]=2[CH:3]=1.[CH3:25][O:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][C:32]=1[O:33][CH3:34].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].COCCOC>[CH3:25][O:26][C:27]1[CH:28]=[C:29]([C:2]2[CH:11]=[N:10][C:9]3[N:8]([CH2:12][C:13]4[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=4)[C:7](=[O:21])[N:6]4[N:22]=[CH:23][N:24]=[C:5]4[C:4]=3[CH:3]=2)[CH:30]=[CH:31][C:32]=1[O:33][CH3:34]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

9-Bromo-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 1, 75 mg, 0.19 mmol), 3,4-dimethoxyphenylboronic acid (75 mg, 0.41 mmol), potassium phosphate (104 mg, 0.49 mmol) and DME (3 mL) were combined and nitrogen was bubbled through for 10 minutes. Pd2(dba)3 (13 mg, 0.01 mmol) was added and the mixture was heated for 2 h at 120° C. in the microwave. Purification (HPLC, 10-80% ACN-water) afforded the title compound (6 mg, 7%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 3.76 (s, 3H), 3.96 (s, 3H), 3.99 (s, 3H), 5.78 (s, 2H), 6.83-6.84 (m, 2H), 7.02 (d, J=6.7 Hz, 1H), 7.15 (d, J=1.6 Hz, 1H), 7.24 (dd, J=6.7, 1.5 Hz, 1H), 7.62-7.64 (m, 2H), 8.37 (s, 1H), 8.76 (d, J=1.9 Hz, 1H), 8.99 (d, J=1.9 Hz, 1H). [M+H]=444.2.

Aufarbeitung

customnitrogen was bubbled through for 10 minutes
customPurification (HPLC, 10-80% ACN-water)

Quellen und Nachweise

ORD-Eintrag: ord-98b1c177f1af4214ae93e9e4b533285e
Quelldatensatz: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09284335B2

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