3-Bromo-4-fluorobenzaldehyde → HCID 9908610, compound

HRID 1837075Notes

Reaction equation

HRID 1837075 reaction equation
[O:1]1[CH2:6][C:5](=O)[CH2:4][C:3](=[O:8])[CH2:2]1.[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>C(O)C>[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:5]3[CH2:6][O:1][CH2:2][C:3](=[O:8])[C:4]2=3)[CH:15]=[CH:16][C:17]=1[F:18]

Participants

5

Reactant 3

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-oneHCID 3252872H-pyran-3,5(4H,6H)-dione

Product 1

HCID 9908610HCID 9908610, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2H-Pyran-3,5(4H,6H)-dione (0.34 g, 3 mmol), 3-bromo-4-fluoro-benzaldehyde (0.61 g, 3 mmol), and 5-amino-1-methyl-1,2-dihydropyrazol-3-one (0.34 g, 3 mmol) in ethyl alcohol (6 mL) were heated at 80° C. for 2 days in a sealed tube. The reaction mixture was cooled and the resulting precipitate was filtered off to provide 0.55 g (46%) of the title compound as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 3.5 (s, 3H), 4.1 (s, 2H), 4.53 (q, 2H), 4.98 (s, 1H), 7.18 (m, 1H), 7.21 (t, 1H), 7.4 (dd, 1H), 9.65 (bs, 1H), 10.52 (s, 1H); MS (ESI−) m/z 394,392 (M−H)−; Anal. calcd for C16H13N3BrFO3: C, 49.11; H, 4.35; N, 9.54. Found: C, 49.08; H, 3.83; N, 9.35.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-e70e9aa5aec14d1e9a0eb355b966dcda
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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