3-Bromo-4-fluorobenzaldehyde → HCID 23497545, compound

HRID 1837085Notes

Reaction equation

HRID 1837085 reaction equation
[C:1]([O:4][CH2:5][C:6](=O)[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:3])[CH3:2].[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[F:23])[CH:18]=O.[NH2:24][C:25]1[N:29]([CH3:30])[NH:28][C:27](=[O:31])[CH:26]=1>C(O)C>[C:1]([O:4][CH2:5][C:6]1[NH:24][C:25]2[N:29]([CH3:30])[NH:28][C:27](=[O:31])[C:26]=2[CH:18]([C:17]2[CH:20]=[CH:21][C:22]([F:23])=[C:15]([Br:14])[CH:16]=2)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-oneHCID 11480907Ethyl 4-acetoxyacetoacetate

Product 1

HCID 23497545HCID 23497545, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 4-(acetyloxy)-3-oxobutanoate (0.19 g, 1 mmol), prepared as described in (S. Husband, W. Fraser, C. J. Suckling, H. C. Wood, Tetrahedron, (1995) 51(3), 865), 3-bromo-4-fluorobenzaldehyde (0.2 g, 1 mmol) and 5-amino-1-methyl-1,2-dihydropyrazol-3-one (0.11 g, 1 mmol) in ethyl alcohol (3 mL) were heated at 80° C. for 24 hours in a sealed tube. The reaction mixture was evaporated under reduced pressure and chromatographed on silica gel eluting with 5% ethanol/methylene chloride to provide 0.1 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 1.03 (t, 3H), 2.1 (s,3H), 3.46 (s, 3H), 3.92 (q, 2H), 4.95 (s, 1H), 5.12 (q, 2H), 7.18 (m, 1H), 7.22 (t, 1H), 7.38 (dd, 1H), 9.43 (s, 1H); MS (ESI−) m/z 468 (M−H)−.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customchromatographed on silica gel eluting with 5% ethanol/methylene chloride

Sources & evidence

ORD record
ord-092ac9ae5f1a4bc49ed7904de55e3312
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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