N-bromobutanimide → 7-(1-Bromo-8-chloroimidazo[1,5-a]pyrazin-3-yl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine

HRID 62478Notes

Reaction equation

HRID 62478 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:11]3[CH2:16][CH2:15][N:14]4[C:17]([C:20]([F:23])([F:22])[F:21])=[N:18][N:19]=[C:13]4[CH2:12]3)=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.C1C(=O)N([Br:31])C(=O)C1>CN(C=O)C>[Br:31][C:10]1[N:9]=[C:8]([CH:11]2[CH2:16][CH2:15][N:14]3[C:17]([C:20]([F:22])([F:21])[F:23])=[N:18][N:19]=[C:13]3[CH2:12]2)[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([Cl:1])[C:3]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 903040007-(8-Chloroimidazo[1,5-a]pyrazin-3-yl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 903039897-(1-Bromo-8-chloroimidazo[1,5-a]pyrazin-3-yl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridineYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(8-chloroimidazo[1,5-a]pyrazin-3-yl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine (335 mg, 0.978 mmol) in DMF (4.9 mL) was added NBS (226.19 mg, 1.271 mmol) at ice water, the resulting solution was stirred at this temperature for 10 minutes. The reaction was quenched with water, then extracted with EA and the combined organic layer was washed with water, brine and dried over anhydrous Na2SO4. The organic layer was concentrated in vacuo to give 7-(1-bromo-8-chloroimidazo[1,5-a]pyrazin-3-yl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine (0.41 g, yield 99%).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EA
  3. washthe combined organic layer was washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-592aede79fc24546b0bb8af1b3bc24a1
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Reaction notes

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