N-bromobutanimide → HCID 18446605, compound

HRID 1269077Notes

Reaction equation

HRID 1269077 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:13]3[O:14][CH:15]=[CH:16][CH:17]=3)[C:10]([CH:11]=[O:12])=[C:6]2[CH:5]=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>ClCCl>[Br:18][C:15]1[O:14][C:13]([C:9]2[C:10]([CH:11]=[O:12])=[C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]3[N:8]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18446628HCID 18446628, compound

Product 1

HCID 18446605HCID 18446605, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-chloro-2-(2-furyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde (2.0 g, 8.06 mmol) in dichloromethane was added N-bromosuccinimide (2.01 g, 11.28 mmol). After stirring at room temperature for 2 hours, the reaction mixture was diluted with dichloromethane, washed with water and brine and dried over magnesium sulfate. Filtration and concentration followed by recrystallization with ethyl acetate gave 2-(5-bromo-2-furyl)-7-chloropyrazolo[1,5-a]pyridine-3-carbaldehyde (2.1 g, 80%) as a white solid. 1H NMR (CDCl3): δ 10.50 (s, 1H), 8.37 (dd, 1H), 7.47 (t, 1H), 7.20–7.18 (m, 2H), 6.54 (d, 1H). MS m/z 325 (M+1).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationFiltration and concentration
  4. customfollowed by recrystallization with ethyl acetate

Sources & evidence

ORD record
ord-3e7db95745b4477f840bc10309f2dddd
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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