3-Bromo-4-fluorobenzaldehyde → HCID 10294856, compound

HRID 1837102Notes

Reaction equation

HRID 1837102 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])[N:23]([CH3:26])[C:22](=[O:27])[CH:21]=1>C(O)C>[Br:9][C:10]1[CH:11]=[C:12]([CH:13]2[C:21]3[C:22](=[O:27])[N:23]([CH3:26])[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 3252872H-pyran-3,5(4H,6H)-dioneHCID 23497515HCID 23497515, compound

Product 1

HCID 10294856HCID 10294856, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2H-Pyran-3,5-(4H,6H)-dione (0.08 g, 0.7 mmol), 3-bromo-4-fluorobenzaldehyde (0.14 g, 0.7 mmol), and 5-amino-1,2-dimethyl-1,2-dihydro-3H-pyrazol-3-one (0.09 g, 0.7 mmol) in ethyl alcohol (2 mL) were heated at 80° C. for 24 hours in a sealed tube. The reaction mixture was allowed to cool to ambient temperature and then filtered to provide the title compound (0.11 g). 1H NMR (300 MHz, DMSO-d6) δ 3.0 (s,3H), 3.12 (s, 3H), 4.12 (s, 1H), 4.52 (q, 2H), 4.78 (s, 1H), 7.23 (m, 2H), 7.48 (dd, 1H), 10.18 (s, 1H); MS (ESI−) m/z 408 (M−H)−.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-55c68f4dae074c519e51d754e84bcff2
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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