Hydrochloric Acid → 7-[(3-fluorophenyl)sulfonyl]-3,4,5',6'-tetrahydro-2H,4'H-spiro[1-benzofuro[2,3-c]pyridine-1,3'-pyran]

To a solution of 7-[(3-fluorophenyl)sulfanyl]-3,4,5′,6′-tetrahydro-2H,4′H-spiro[1-benzofuro[2,3-c]pyridine-1,3′-pyran] (0.160 g, 0.433 mmol) in methanol (5.0 mL, 120 mmol) was added a solution of Oxone® (0.666 g, 1.08 mmol) in water (5.0 mL, 280 mmol) and the mixture was stirred at rt overnight. After 3 h, the reaction mixture was filtered, concentrated, and then extracted with DCM/sat. aq. NaHCO3. The extract was dried, concentrated and then purified by silica gel chromatography (DCM-MeOH—NH4OH) to afford an off-white solid. The product was converted to the HCl salt using excess EtOH—HCl and dried overnight at 80° C. under high vacuum. mp 285-290° C. dec.; MS m/z 401 [M+H]+. 1H-NMR (400 MHz, CDCl3): d 1.7 (d, J=12.6 Hz, 1H), 1.83 (d, J=14.2 Hz, 1H), 2.0 (m, 2H), 2.3 (m, 1H), 2.7 (m, 2H), 3.2 (m, 2H), 3.6 (m, 1H), 3.7 (d, J=11.5 Hz, 1H), 3.85 (d, J=12 Hz, 1H), 4.0 (d, J=10.6 Hz, 1H), 7.2 (m, 2H), 7.4 (m, 1H), 7.57 (d, J=8.1 Hz, 1H), 7.66 (d, J=8.1 Hz, 1H), 7.76 (d, J=8.1 Hz, 1H), 7.82 (d, J=8.2 Hz, 1H), 8.08 (s, 1H).

1. waitAfter 3 h
2. filtrationthe reaction mixture was filtered
3. concentrationconcentrated
4. extractionextracted with DCM/
5. customThe extract was dried
6. concentrationconcentrated
7. custompurified by silica gel chromatography (DCM-MeOH—NH4OH)
8. customto afford an off-white solid
9. customdried overnight at 80° C. under high vacuum

ORD record

ord-2b7bc5edb3eb4da5b24e0ec82aec6c7e

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765779B2