Cesium carbonate → HCID 67393000, compound

HRID 913352Notes

Reaction equation

HRID 913352 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[S:14][C:13]([CH2:15][CH2:16][CH3:17])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1>CN(C=O)C>[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][O:1][C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[S:14][C:13]([CH2:15][CH2:16][CH3:17])=[N:12][C:7]=4[CH:8]=[N:9][C:10]=3[CH:11]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680214-Fluorobenzyl bromideHCID 136367418HCID 136367418, compound

Product 1

HCID 67393000HCID 67393000, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-hydroxy-2-propylthiazolo[4,5-c]quinoline (0.88 g, 3.6 mmol) and cesium carbonate (2.35 g, 7.20 mmol) in DMF (50 mL) was stirred for 30 min, then 4-fluorobenzylbromide (0.50 mL, 4.0 mmol) was added. After 2 h, the mixture was concentrated in vacuo to remove the DMF. The resulting solid was partitioned between dichloromethane (100 mL) and water (100 mL). The organic layer was washed with water (50 mL) and brine (50 mL), dried over MgSO4, filtered, and concentrated to a light yellow solid. The solid was recrystallized from heptane and pure 7-(4-fluorobenzyloxy)-2-propylthiazolo[4,5-c]quinoline was isolated as a tan solid (0.86 g, 68%).

Workup

  1. waitAfter 2 h
  2. concentrationthe mixture was concentrated in vacuo
  3. customto remove the DMF
  4. customThe resulting solid was partitioned between dichloromethane (100 mL) and water (100 mL)
  5. washThe organic layer was washed with water (50 mL) and brine (50 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to a light yellow solid
  9. customThe solid was recrystallized from heptane

Sources & evidence

ORD record
ord-733c48ad6b2043c891fa94af1eeccb5e
Source dataset
uspto-grants-2011_09
Patent number
US08026366B2

Reaction notes

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