N-bromobutanimide → HCID 68265200, compound

HRID 245667Notes

Reaction equation

HRID 245667 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:11]3[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:17])[CH2:12]3)=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.[Br:26]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>CN(C)C=O>[Br:26][C:10]1[N:9]=[C:8]([C@@H:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[CH2:12]2)[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([CH3:1])[C:3]=12

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 86674636HCID 86674636, compound

Product 1

HCID 68265200HCID 68265200, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (R)-benzyl 3-(8-methylimidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate (1.332 mmol, 448 mg) in N,N-dimethylformamide (5 ml) was added N-bromosuccinimide (1.332 mmol, 237 mg). After stirring at room temperature for five minutes saturated aqueous sodium hydrogencarbonate solution was added, the organic layer was separated and the aqueous layer extracted three times with ethyl acetate. The combined organic layers were washed with water, brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by column chromatography (silica gel; dichloromethane/methanol (gradient 0 to 10% methanol)) to give (R)-benzyl 3-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate (531 mg).

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. extractionthe aqueous layer extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel; dichloromethane/methanol (gradient 0 to 10% methanol))

Sources & evidence

ORD record
ord-4f54d43d179c47f4adb9504c3be6393f
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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