N-bromobutanimide → Methyl 5-bromo-1-isopropyl-1H-pyrrole-3-carboxylate

HRID 2204300Notes

Reaction equation

HRID 2204300 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][O:10][C:11]([C:13]1[CH:17]=[CH:16][N:15]([CH:18]([CH3:20])[CH3:19])[CH:14]=1)=[O:12]>C(Cl)(Cl)(Cl)Cl>[CH3:9][O:10][C:11]([C:13]1[CH:17]=[C:16]([Br:8])[N:15]([CH:18]([CH3:20])[CH3:19])[CH:14]=1)=[O:12]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86703103Methyl 1-isopropyl-1H-pyrrole-3-carboxylate

Product 1

HCID 86703102Methyl 5-bromo-1-isopropyl-1H-pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

NBS (36.6 mmol) was added to a mixture of 1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester (Step D5) (37.4 mmol) in CCl4 (250 mL). After 4 h, the reaction mixture was successively washed with a saturated aqueous solution of NaHCO3, water and brine, dried (Na2SO4), filtered and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as a pale yellow-pink oil. tR: 4.56 min (HPLC 1); ESI-MS: tR=1.13 min, [M+H]+ 246/248 (LC-MS 1); TLC: Rf=0.35 (1:6 EtOAc/heptanes).

Workup

  1. washthe reaction mixture was successively washed with a saturated aqueous solution of NaHCO3, water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-c452d7751ac04dc9bb56d0c3d7ec276b
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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