Sodium Iodide → HCID 117856952, compound

HRID 509897Notes

Reaction equation

HRID 509897 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][CH:8]1[CH2:12][CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[C:1]([O:5][C:6](=[O:13])[NH:7][CH:8]1[CH2:12][CH2:11][N:10]([CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 127769961-(3-Bromopropyl)-4-methoxybenzene

Product 1

HCID 117856952HCID 117856952, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Pyrrolidin-3-yl-carbamic acid tert-butyl ester (250 mg, 1.35 mmol) and 1-(3-Bromo-propyl)-4-methoxy-benzene (375 μl, 2.15 mmol), potassium carbonate (550 mg, 4 mmol) and sodium iodide (50 mg, 0.33 mmol) are dissolved in acetonitril and stirred at reflux overnight. The reaction is filtered and purified by preparative HPLC-MS (MeOH/H2O+0.1% TFA). 2 M K2CO3 is added to relevant fractions to prevent cleavage of boc group during solvent evaporation. Methanol is removed under reduced pressure and the remaining aqueous phase is extracted with dichloromethane. The solvent is removed in vacuo. LC (method F): tR=1.61 min; Mass spectrum (ESI+): m/z=335 [M+H]+.

Workup

  1. temperatureat reflux overnight
  2. filtrationThe reaction is filtered
  3. custompurified by preparative HPLC-MS (MeOH/H2O+0.1% TFA)
  4. addition2 M K2CO3 is added to relevant fractions
  5. customduring solvent evaporation
  6. customMethanol is removed under reduced pressure
  7. extractionthe remaining aqueous phase is extracted with dichloromethane
  8. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-0180bf8f05334f2f832347ba3ce353bf
Source dataset
uspto-grants-2015_08
Patent number
US09096548B2

Reaction notes

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