N-Bromosuccinamide → 3-bromo-2-(6-methylpyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

HRID 8234Notes

Reaction equation

HRID 8234 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[C:9](C(O)=O)=[C:10]3[CH2:15][CH2:14][CH2:13][N:11]3[N:12]=2)[CH:5]=[CH:4][CH:3]=1.[Br:19]NC(=O)CCC(N)=O>CN(C)C=O.C(OCC)(=O)C>[Br:19][C:9]1[C:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=2)=[N:12][N:11]2[CH2:13][CH2:14][CH2:15][C:10]=12

Participants

5

Reactant 2

HCID 9834204N-BromosuccinamideHCID 219925742-(6-methylpyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid

Product 1

HCID 99002873-bromo-2-(6-methylpyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid (1.4 g, 5.8 mmol) in N,N-dimethylformamide (20 mL) is treated with N-bromosuccinamide (1 g, 5.6 mmol) and stirred at room temperature for 16 h. The mixture is diluted with ethyl acetate and washed three times with water, once with brine, dried (sodium sulfate), filtered, and concentrated in vacuo to yield the title compound, 1.5 g (94%), as light yellow solid.

Workup

  1. washwashed three times with water
  2. dry with materialonce with brine, dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-89e061fe72f54d6990f195745c8d82e2
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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