Potassium Carbonate → HCID 21895242, compound

HRID 1069148Notes

Reaction equation

HRID 1069148 reaction equation
[CH3:1][CH:2]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])[CH:3](OS(C)(=O)=O)[CH3:4].[Cl:21][C:22]1[CH:23]=[C:24]([C:28]#[N:29])[NH:25][C:26]=1[CH3:27].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOCC>[Cl:21][C:22]1[CH:23]=[C:24]([C:28]#[N:29])[N:25]([CH2:4][CH2:3][CH:2]([N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])[CH3:1])[C:26]=1[CH3:27]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 218952722-[1-methyl-2-[(methylsulfonyl)oxy]propyl]-1H-isoindole-1,3(2H)-dioneHCID 21895281HCID 21895281, compound

Product 1

HCID 21895242HCID 21895242, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4.23 g (14.2 mmol) of 2-[1-methyl-2-[(methylsulfonyl)oxy]propyl]-1H-isoindole-1,3(2H)-dione, 2.05 g (14.2 mmol) of 4-chloro-5-methyl-1H-pyrrole-2-carbonitrile and 2.35 g (14.2 mmol) of K2CO3 in 60 mL DMF was heated at 60° C. overnight. The mixture was diluted with ether and washed 4 times with water. Drying (MgSO4) and removal of solvent gave an oil which was chromatographed on silica gel (15% ethyl acetate in hexanes) to give 3.2 g of 4-chloro-1-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butyl]-5-methyl-1H-pyrrole-2-carbonitrile as a solid, 1NMR (CDCl3) δ 1.5 (d, 3H) 2.2 (s, 3H and m, 1H), 2.7 (m, 1H), 3.9 (m, 1H), 4.05 (m, 1H), 4.4 (m, 1H), 6.6 (s, 1H), 7.85 (m, 2H), 7.9 (m, 2H).

Workup

  1. washwashed 4 times with water
  2. customDrying
  3. custom(MgSO4) and removal of solvent
  4. customgave an oil which
  5. customwas chromatographed on silica gel (15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3619d6ce288f44ca950691bf413f9349
Source dataset
uspto-grants-2001_06
Patent number
US06251947B1

Reaction notes

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