Benzyl Chloride → HCID 59754358, compound

HRID 501579Notes

Reaction equation

HRID 501579 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH:8]=[CH:7]2)([O-:3])=[O:2].[F-].[Cs+].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:9](=[O:14])[CH:8]=[CH:7]2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 25953Cesium fluorideHCID 8999326-Nitroquinolin-2(1H)-one

Product 1

HCID 59754358HCID 59754358, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 46B (50 mg, 0.26 mmol) was dissolved in DMF (1 mL), CsF (120 mg, 0.79 mmol) and benzyl chloride (0.09 mL, 0.79 mmol) were added, and the reaction was stirred at rt for 16 h. The reaction mixture was then concentrated under reduced pressure and subsequently purified by silica gel flash chromatography eluting with 0-5% EtOAc/CH2Cl2 (gradient) to give the title compound (57 mg, 77%). LC/MS m/z 281 [M+H]+.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customsubsequently purified by silica gel flash chromatography
  3. washeluting with 0-5% EtOAc/CH2Cl2 (gradient)

Sources & evidence

ORD record
ord-a776675dbb9d4e20b661bee69d749aad
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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