Potassium Carbonate → HCID 21895242, compound

HRID 1271453Notes

Reaction equation

HRID 1271453 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) δ1.5 (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-b171f717edbe44989b21b5fb1622b852
Source dataset
uspto-grants-2007_04
Patent number
US07205331B2

Reaction notes

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