Iodoethane → 8-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-ethyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

HRID 445781Notes

Reaction equation

HRID 445781 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:23])[C:13](=[O:22])[N:14]([C:15]4[C:16]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[H-].[Na+].I[CH2:27]C>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH2:23][CH3:27])[C:13](=[O:22])[N:14]([C:15]4[C:16]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 596197398-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

Product 1

HCID 596200728-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-ethyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Stage A.1, 0.698 mmol) in DMF (5 ml) cooled with an ice-bath was added 55% NaH in oil (1.398 mmol). The RM was stirred for 30 min at rt then was added iodoethane (0.085 ml) and the RM was stirred for 30 min at rt. The RM was diluted with EtOAc and washed with saturated aqueous NaHCO3, with brine (2×), dried over Na2SO4, filtered and evaporated. The residue was absorbed on silica gel and purified by flash chromatography (CH2Cl2/MeOH 0% to 3.5%). The fractions containing product were evaporated together to give the title compound as a brown solid. (HPLC: tR 2.41 min (Method A); M+H=386, 388 MS-ES)

Workup

  1. stirringthe RM was stirred for 30 min at rt
  2. washwashed with saturated aqueous NaHCO3, with brine (2×)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was absorbed on silica gel
  7. custompurified by flash chromatography (CH2Cl2/MeOH 0% to 3.5%)
  8. additionThe fractions containing product
  9. customwere evaporated together

Sources & evidence

ORD record
ord-8bf3743c164440dbb0f9f0d6db527bd5
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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