Isopropyl iodide → HCID 58577296, compound

HRID 1429966Notes

Reaction equation

HRID 1429966 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[NH:19][C:18]2=[O:26])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH:28]([CH3:30])[CH3:29].[Cl-].[Cl-].[Ca+2]>CN(C=O)C.CO>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([N:17]2[C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[N:19]([CH:28]([CH3:30])[CH3:29])[C:18]2=[O:26])=[CH:15][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 5284359Calcium ChlorideHCID 585776613-[4-(benzyloxy)phenyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 58577296HCID 58577296, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

NaH (1.260 g) was added to a solution of 3-[4-(benzyloxy)phenyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (5 g) and 2-iodopropane (3.15 mL) in DMF (50 mL) at room temperature. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 1 h. The reaction mixture was diluted with MeOH and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 0%-50% EtOAc in hexane) to give 3-[4-(benzyloxy)phenyl]-1-(1-methylethyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1.5 g) as dark yellow oil.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (NH silica gel, eluted with 0%-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-c6ca98161aa645de829986c87f43bc95
Source dataset
uspto-grants-2015_01
Patent number
US08940758B2

Reaction notes

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