N-bromobutanimide → 4-(6-Amino-5-bromopyridin-3-yl)-1-methylpyrrolidin-2-one

HRID 595925Notes

Reaction equation

HRID 595925 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:12][N:11]([CH3:13])[C:10](=[O:14])[CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:22])C(=O)C1.C(=O)(O)[O-].[Na+]>C(#N)C.CCOC(C)=O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:12][N:11]([CH3:13])[C:10](=[O:14])[CH2:9]2)=[CH:4][C:3]=1[Br:22]

Participants

6

Reactant 3

HCID 67184N-bromobutanimide2×HCID 516892Sodium BicarbonateHCID 1180470204-(6-Aminopyridin-3-yl)-1-methylpyrrolidin-2-one

Product 1

HCID 1180455874-(6-Amino-5-bromopyridin-3-yl)-1-methylpyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-(6-aminopyridin-3-yl)-1-methylpyrrolidin-2-one (90 mg, 0.377 mmol) in Acetonitrile 3 mL) in ice bath was added NBS (60.3 mg, 0.339 mmol). The reaction mixture was stirred in ice bath for 15 min and room temperature for 30 min. LC-MS shows mixture of SM and product. Added 0.1 equiv. more of NBS and stirred another 1h at room temperature. Reaction mixture was diluted with EtOAc and added 2 mL of Satd sodium bicarbonate. Stirred 10 min. The organic layer was separated, dried over sodium sulfate, filtered and evaporated. Proceed for next step (73%). LCMS (m/z): 270.2/272.2 (MH+), 0.302 min.

Workup

  1. waitroom temperature for 30 min
  2. additionmixture of SM and product
  3. customReaction mixture
  4. stirringStirred 10 min
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. custom270.2/272.2 (MH+), 0.302 min.

Sources & evidence

ORD record
ord-2ce8528b38cf46b690634c6c82f7413d
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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