Benzyl Bromide → HCID 58562523, compound

HRID 1896940Notes

Reaction equation

HRID 1896940 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[N:7][CH:6]=[C:5]2[OH:12].Br[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[CH2:14]([O:12][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([I:1])[CH:3]=2)[N:8]=[N:7][CH:6]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 178516804HCID 178516804, compound

Product 1

HCID 58562523HCID 58562523, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Into a 250 mL round-bottom flask, was placed a solution of 6-iodocinnolin-4-ol (as prepared in the previous step, 6.5 g, 23.90 mmol, 1.00 equiv) in N,N-dimethylformamide (120 mL), 1-(bromomethyl)benzene (4.4 g, 25.88 mmol, 1.10 equiv) and Cs2CO3 (5.47 g, 16.78 mmol, 0.70 equiv). The reaction mixture was stirred for 3 h at 60° C. in an oil bath. The reaction was then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3×100 ml, of ethyl acetate, and the combined organic layers washed with 2×100 mL of sodium chloride, dried (Na2SO4), and concentrated under vacuum. The title compound was obtained as a yellow solid.

Workup

  1. customInto a 250 mL round-bottom flask, was placed
  2. customThe reaction was then quenched by the addition of 50 mL of water
  3. extractionThe resulting solution was extracted with 3×100 ml, of ethyl acetate
  4. washthe combined organic layers washed with 2×100 mL of sodium chloride
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-17f148c8f733447a90f4ba04e14c832c
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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