Isopropyl iodide → HCID 90093468, compound

HRID 1753049Notes

Reaction equation

HRID 1753049 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]2[C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:13]=3[NH:12][CH:11]=2)=[O:9])[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].I[CH:26]([CH3:28])[CH3:27]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]2[C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:13]=3[N:12]([CH:26]([CH3:28])[CH3:27])[CH:11]=2)=[O:9])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 90094001HCID 90094001, compound

Product 1

HCID 90093468HCID 90093468, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (2-chloropyridin-4-yl)-(1H-pyrrolo[3,2-c]pyridin-3-yl)methanone (Preparation 49, 34 g, 0.13 mol) in DMF (700 mL) was added Cs2CO3 (65 g, 0.2 mol) and 2-iodopropane (34 g, 0.2 mol) at room temperature and the reaction stirred for 18 hours. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate from 10:1 to 1:1 to afford the title compound as a yellow solid (7.7 g, 23.6%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by silica gel column chromatography
  3. washeluting with petroleum ether/ethyl acetate from 10:1 to 1:1

Sources & evidence

ORD record
ord-222eb9d2ef7645e881d44e4a05703380
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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