Potassium Carbonate → HCID 21895242, compound

HRID 478986Notes

Reaction equation

HRID 478986 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-fd2b330aa6824138bda538ff5950c291
Source dataset
uspto-grants-2003_11
Patent number
US06642392B1

Reaction notes

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