Potassium Phosphate, Tribasic → 5-[3,4-Dimethoxy-2-(3-methoxymethyl-oxetan-3-ylmethoxy)-phenyl]-3H-isobenzofuran-1-one

HRID 2171054Notizen

Reaktionsgleichung

Br[C:2]1[C:7]([O:8][CH2:9][C:10]2([CH2:14][O:15][CH3:16])[CH2:13][O:12][CH2:11]2)=[C:6]([O:17][CH3:18])[C:5]([O:19][CH3:20])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:29]2[CH:30]=[C:31]3[C:35](=[CH:36][CH:37]=2)[C:34](=[O:38])[O:33][CH2:32]3)O1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.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]>[CH3:18][O:17][C:6]1[C:7]([O:8][CH2:9][C:10]2([CH2:14][O:15][CH3:16])[CH2:13][O:12][CH2:11]2)=[C:2]([C:29]2[CH:30]=[C:31]3[C:35](=[CH:36][CH:37]=2)[C:34](=[O:38])[O:33][CH2:32]3)[CH:3]=[CH:4][C:5]=1[O:19][CH3:20]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

3-(6-Bromo-2,3-dimethoxy-phenoxymethyl)-3-methoxymethyl-oxetane (0.02 g, 0.06 mmol) and 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3H-isobenzofuran-1-one (Compound 309) (0.039 g, 0.14 mmol) were dissolved in 1,4-dioxan (0.6 mL). Argon was purged through the solution. Pd2(dba)3 0.001 g, 0.001 mmol) and PCy3 (0.0008 g, 0.003 mmol) were added followed by addition of K3PO4 (0.043 g, 0.2 mmol) in H2O (0.3 mL). The reaction mixture was heated in a microwave oven at 120° C. for 10 min. The mixture was filtrated, concentrated, redissolved in DMSO and purified by preparative HPLC to afford the title compound.

Aufarbeitung

customArgon was purged through the solution
filtrationThe mixture was filtrated
concentrationconcentrated
dissolutionredissolved in DMSO
custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-dba926f8a132457aabb4d3dc77642056
Quelldatensatz: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09051290B2

Notizen zur Reaktion

Wird geladen…