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

HRID 1862436Notes

Reaction equation

HRID 1862436 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][C:2]1=[O:8].[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH:13]=O.[NH2:19][C:20]1[N:24]([CH3:25])[NH:23][C:22](=[O:26])[CH:21]=1>>[Br:9][C:10]1[CH:11]=[C:12]([CH:13]2[C:21]3[C:22](=[O:26])[NH:23][N:24]([CH3:25])[C:20]=3[NH:19][C:4]3[CH2:5][CH2:6][O:1][C:2](=[O:8])[C:3]2=3)[CH:15]=[CH:16][C:17]=1[F:18]

Participants

4

Reactant 3

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-oneHCID 9793733Oxane-2,4-dione

Product 1

HCID 101787204-(3-Bromo-4-fluorophenyl)-1-methyl-1,2,4,7,8,9-hexahydropyrano[4,3-b]pyrazolo[4,3-e]pyridine-3,5-dioneYield 68.5%

Procedure

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.

Sources & evidence

ORD record
ord-db9a32c26ec8492fbffee359beeafca0
Source dataset
uspto-grants-2003_03
Patent number
US06538004B2

Reaction notes

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