Pyrrolidine → HCID 71284829, compound

HRID 1481741Notes

Reaction equation

HRID 1481741 reaction equation
[CH3:1][O:2][C:3]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:4]=1[CH2:5][N:6]1[C:11]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[C:16]([CH2:22][CH2:23]OS(C)(=O)=O)=[CH:15]3)=[C:10]([CH2:29][CH3:30])[CH:9]=[C:8]([C:31]([O:33][CH3:34])=[O:32])[C:7]1=[O:35].[NH:42]1[CH2:46][CH2:45][CH2:44][CH2:43]1.C([O-])(O)=O.[Na+]>CC#N>[CH3:1][O:2][C:3]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:4]=1[CH2:5][N:6]1[C:11]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[C:16]([CH2:22][CH2:23][N:42]2[CH2:46][CH2:45][CH2:44][CH2:43]2)=[CH:15]3)=[C:10]([CH2:29][CH3:30])[CH:9]=[C:8]([C:31]([O:33][CH3:34])=[O:32])[C:7]1=[O:35]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 89422916HCID 89422916, compound

Product 1

HCID 71284829HCID 71284829, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To solution of methyl 1-(2,4-dimethoxybenzyl)-5-ethyl-6-(1-methyl-2-(2-(methylsulfonyloxy)ethyl)-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylate (0.233 g, 0.40 mmol) in CH3CN (2 mL) was added pyrrolidine (0.15 mL, 1.83 mmol). Reaction mixture was heated at 80° C. for 1.5 h until complete consumption of starting material was observed. Then NaHCO3 (aqueous saturated, 5 mL) was added to the reaction and product was extracted with DCM (3×10 mL). Combined organics were washed with NaCl (aqueous saturated, 5 mL) and dried over Na2SO4. Upon solvent removal residue was purified by column chromatography using MeOH/DCM (gradient 0-10%) to afford methyl 1-(2,4-dimethoxybenzyl)-5-ethyl-6-(1-methyl-2-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylate (0.140 g) in 62% yield.

Workup

  1. customReaction mixture
  2. extractionwas extracted with DCM (3×10 mL)
  3. washCombined organics were washed with NaCl (aqueous saturated, 5 mL)
  4. dry with materialdried over Na2SO4
  5. customUpon solvent removal residue
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-f053b50ab12f4f98b0b30f1e35472f02
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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