Isopropyl iodide → HCID 11589308, compound

HRID 907153Notes

Reaction equation

HRID 907153 reaction equation
O=S1(=O)CCCN1C1C=CC(C2N(CC)C3C(C=2C#N)=CC=C(O)C=3)=CC=1.C([O-])([O-])=O.[K+].[K+].IC(C)C.[O:38]=[S:39]1(=[O:67])[CH2:43][CH2:42][CH2:41][N:40]1[C:44]1[CH:49]=[CH:48][C:47]([C:50]2[N:51]([CH2:65][CH3:66])[C:52]3[C:57]([C:58]=2[C:59]#[N:60])=[CH:56][CH:55]=[C:54]([O:61][CH:62](C)C)[CH:53]=3)=[CH:46][CH:45]=1>CCOC(C)=O.C(Cl)Cl.C(C(C)=O)C>[O:67]=[S:39]1(=[O:38])[CH2:43][CH2:42][CH2:41][N:40]1[C:44]1[CH:45]=[CH:46][C:47]([C:50]2[N:51]([CH2:65][CH3:66])[C:52]3[C:57]([C:58]=2[C:59]#[N:60])=[CH:56][CH:55]=[C:54]([O:61][CH3:62])[CH:53]=3)=[CH:48][CH:49]=1

Participants

7

Reactant 4

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 59425169HCID 59425169, compoundHCID 59426360HCID 59426360, compound

Product 1

HCID 11589308HCID 11589308, compound

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Following the procedure in example 1B step B, 2-[4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl]-1-ethyl-6-hydroxy-1H-indole-3-carbonitrile, K2CO3, 2-iodopropane and methyl ethyl ketone were heated at reflux to give, after flash chromatography (EtOAc/CH2Cl2, 0-2%), 61% of 2-[4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl]-1-ethyl-6-isopropoxy-1H-indole-3-carbonitrile as an off-white solid.

Workup

  1. temperaturewere heated
  2. temperatureat reflux
  3. customto give

Sources & evidence

ORD record
ord-3c32714e8a5840e78c26f39ad6ee78fd
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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