Potassium Carbonate → HCID 136052226, compound

HRID 884662Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH2:17][O:18][CH3:19])=[C:6]([C:8](=O)[CH2:9][C:10](=[O:14])COC)[CH:7]=1.[ClH:20].[C:21]([NH2:29])(=[NH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].OS([O-])(=O)=O.[Na+]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH2:17][O:18][CH3:19])=[C:6]([C:8]2[N:29]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:20])[NH:28][C:10](=[O:14])[CH:9]=2)[CH:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A 100-mL round bottom flask was charged with 1-(5-bromo-2-(methoxymethoxy)phenyl)-4-methoxybutane-1,3-dione (16, 780 mg, 2.36 mmol), benzamidine hydrochloride (457 mg, 2.39 mmol), potassium carbonate (705 mg, 5.10 mmol) and anhydrous dioxane (16 mL). The mixture was stirred at 110° C. for 16 h under a nitrogen atmosphere. As the reaction was deemed complete by LC-MS, the mixture was cooled to room temperature and poured onto 1N NaHSO4 (50 mL). Extractions with EtOAc (2×80 mL) followed. The combined organic layers were washed with water (40 mL), brine (30 mL), and then dried over MgSO4. After purification by flash chromatography (96:4 CH2Cl2/CH3OH), the title compound (17) was obtained as colorless oil (574 mg, 57% yield).

Workup

temperaturethe mixture was cooled to room temperature
extractionExtractions with EtOAc (2×80 mL)
washThe combined organic layers were washed with water (40 mL), brine (30 mL)
dry with materialdried over MgSO4
customAfter purification by flash chromatography (96:4 CH2Cl2/CH3OH)

Sources & evidence

ORD record: ord-dbafd8c8170748baacddf8085040c98e
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242129B2

Reaction notes

Loading…