3-Bromo-4-fluorobenzaldehyde → HCID 23497521, compound

HRID 1837070Notes

Reaction equation

HRID 1837070 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[NH:5][C:4](=[O:8])[CH:3]=1.[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH:13]=O.[CH2:19]1[C:25](=O)[CH2:24][S:21](=[O:23])(=[O:22])[CH2:20]1>C(O)C>[Br:9][C:10]1[CH:11]=[C:12]([CH:13]2[C:20]3[S:21](=[O:23])(=[O:22])[CH2:24][CH2:25][C:19]=3[NH:1][C:2]3[N:6]([CH3:7])[NH:5][C:4](=[O:8])[C:3]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 5150067dihydrothiophen-3(2H)-one 1,1-dioxide

Product 1

HCID 23497521HCID 23497521, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Amino-1-methyl-1,2-dihydropyrazol-3-one (0.17 g, 1.5 mmol), 3-bromo-4-fluorobenzaldehyde (0.3 g, 1.5 mmol), and tetrahydrothiophene-3-oxo-1,1-dioxide (0.2 g, 1.5 mmol) in ethyl alcohol (3 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 and washed with ethyl acetate to provide 0.41 g of the title compound as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 2.88 (m, 1H), 3.03 (m,1H), 3.4 (m, 2H), 3.48 (s, 3H), 4.92 (s, 1H), 7.21 (m, 1H), 7.24 (t, 1H), 7.4 (d, 1H), 9.55 (s, 1H), 9.89 (s, 1H); MS (ESI−) m/z 414 (M−H)−; Anal. Calcd for C15H13N3BrFO3S: C, 43.49; H, 3.16; N, 10.14. Found: C, 43.64; H, 3.50; N, 9.84.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe resulting precipitate was filtered off
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-28a110c0c35c4bb8b3642d082c12e08c
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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