3-Bromo-4-fluorobenzaldehyde → 4-(3-Bromo-4-fluorophenyl)-1-methyl-1,2,4,7,8,9-hexahydropyrano[4,3-b]pyrazolo[4,3-e]pyridine-3,5-dione

Participants

Role	Name	HCID	Charge
Reactant	3-Bromo-4-fluorobenzaldehyde	HCID 173604	—
Reactant	5-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-one	HCID 252198	—
Reactant	Oxane-2,4-dione	HCID 9793733	—
Product	4-(3-Bromo-4-fluorophenyl)-1-methyl-1,2,4,7,8,9-hexahydropyrano[4,3-b]pyrazolo[4,3-e]pyridine-3,5-dione	HCID 10178720	68.5%

Reaction Steps

Dihydro-2H-pyran-2,4(3H)-dione(0.11 g, 1 mmol), 3-bromo-4-fluoro-benzaldehyde (0.2 g, 1 mmol) and 5-amino-1-methyl-1,2-dihydropyrazol-3-one (0.12g, 1 mmol) were processed as described in Example 26C to provide 0.27 g of the title compound. 1H NMR (300 MHz, DMSO-d6)6 2.55 (m, 1H), 2.8 (m, 1H), 3.5 (s, 3H), 4.22 (m, 2H), 4.86 (s, 1H), 7.2 (m, 2H), 7.41 (dd, 1H), 9.49 (s, 1H), 9.92 (s, 1H); MS (ESI−) m/z 392 (M−H−) Anal. Calcd for C16H13N3BrFO3.C2HO: C, 49.11;H, 4.35; N, 9.54. Found: C, 48.87;H, 4.24; N, 9.40.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06538004B2
Source dataset	uspto-grants-2003_03
ORD ID	ord-db9a32c26ec8492fbffee359beeafca0
Source note	uspto-grants-2003_03