Potassium Carbonate → HCID 90314813, compound

HRID 1524155Notes

Reaction equation

HRID 1524155 reaction equation
[Br:1][C:2]1[C:3]([SH:8])=[N:4][CH:5]=[CH:6][CH:7]=1.Br[CH:10]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:3]([S:8][CH:14]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 426142173-Bromo-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178527856HCID 178527856, compound

Product 1

HCID 90314813HCID 90314813, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-bromopyridine-2-thiol (0.30 g, 1.6 mmol), tert-butyl 3-bromopyrrolidine-1-carboxylate (0.79 g, 3.2 mmol) and K2CO3 (438 mg, 3.20 mmol) in DMF (12 mL) was stirred at rt for 4 h. The reaction mixture was concentrated to dryness and the residue subjected to FCC purification to give partially purified title compound (1.05 g, 63% purity).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue subjected to FCC purification
  3. customto give partially
  4. custompurified title compound (1.05 g, 63% purity)

Sources & evidence

ORD record
ord-2745c5d79d3047bd9aaebe6140e91886
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

Loading…