Diisopropylethylamine → 5-Bromo-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridine

HRID 1475931Notes

Reaction equation

HRID 1475931 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[N:9]2)[CH:3]=1.C(N(CC)C(C)C)(C)C>ClCCCl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[CH:8]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 682759544-Bromo-2-(3-(4-methoxyphenyl)-2H-azirin-2-yl)pyridine

Product 1

HCID 679814685-Bromo-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridineYield 70%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
175 °C

Procedure

In a 20 mL microwave reactor was placed a solution of 4-bromo-2-(3-(4-methoxyphenyl)-2H-azirin-2-yl)pyridine (1.3 g, 4.3 mmol) and N,N-diisopropylethylamine (375 μL, 2.2 mmol) in 1,2-dichloroethane (10 mL). The mixture was heated to 175° C. for 1 hour. The cooled mixture afforded a precipitate which was filtered and dried under reduced pressure to afford the title compound as a white solid (910 mg, 70%). LCMS m/z 303.0, 305.0 (M+H)+, ret. time=2.88 min.

Workup

  1. customIn a 20 mL microwave reactor was placed
  2. customThe cooled mixture afforded a precipitate which
  3. filtrationwas filtered
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-08fbaf76a0de4cf5bba4f51c67ba5702
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

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