Pentafluorophenyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate → Methyl 2-(4-{[(4-bromo-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-6-chloroisonicotinate

HRID 2233938Notes

Reaction equation

HRID 2233938 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10]C2C(F)=C(F)C(F)=C(F)C=2F)=O)[NH:5][C:6]=1[CH3:7].Cl.[NH2:23][CH:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:31]=[C:32]([CH:37]=[C:38]([Cl:40])[N:39]=2)[C:33]([O:35][CH3:36])=[O:34])[CH2:26][CH2:25]1>CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:23][CH:24]2[CH2:25][CH2:26][N:27]([C:30]3[CH:31]=[C:32]([CH:37]=[C:38]([Cl:40])[N:39]=3)[C:33]([O:35][CH3:36])=[O:34])[CH2:28][CH2:29]2)=[O:10])[NH:5][C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 86608241Pentafluorophenyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate2×HCID 86608260Methyl 2-(4-aminopiperidin-1-yl)-6-chloroisonicotinate hydrochloride salt2×

Product 1

HCID 86608287Methyl 2-(4-{[(4-bromo-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-6-chloroisonicotinateYield 76.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Pentafluorophenyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate (intermediate 17, 1.81 g, 4.90 mmol) and TEA (682 μl, 4.9 mmol) were added to methyl 2-(4-aminopiperidin-1-yl)-6-chloroisonicotinate hydrochloride salt (Intermediate 93; 1.5 g, 4.90 mmol) in anhydrous DMA (10 ml). The mixture was stirred at room temperature 18 h then partitioned between EtOAc and water. The organic layer was washed with water, dried over Na2SO4 and concentrated under vacuum. The solid material was purified by flash chromatography eluting with EtOAc/n-hexanes mixture (7:3) to give the title compound as a brown solid (1.7 g).

Workup

  1. customthen partitioned between EtOAc and water
  2. washThe organic layer was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe solid material was purified by flash chromatography
  6. washeluting with EtOAc/n-hexanes mixture (7:3)

Sources & evidence

ORD record
ord-beee9fc68d4e46b4b3a3e740a012238d
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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