Cesium carbonate → HCID 57590863, compound

HRID 1783755Notes

Reaction equation

HRID 1783755 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]>CS(C)=O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 42818821-Chloro-4-hydroxyisoquinoline

Product 1

HCID 57590863HCID 57590863, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-chloro-4-hydroxyisoquinoline (50 mg, 0.28 mmol, 1.0 equiv), Cs2CO3 (454 mg, 1.39 mmol, 5.0 equiv.), and tert-butyl (2-bromoethyl)carbamate (2-2) (94 mg, 0.42 mmol, 1.5 equiv.) were suspended in anhydrous DMSO (2 mL) and stirred at room temperature. When LCMS indicated the reaction was complete, the crude reaction mixture was purified with reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA present) to yield the product (2-3). LRMS m/z (M+H) 323.1 found, 323.1 required.

Workup

  1. customthe crude reaction mixture
  2. customwas purified with reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA present)

Sources & evidence

ORD record
ord-03519a848bbe4761a45defd94301e86d
Source dataset
uspto-grants-2009_03
Patent number
US07501435B2

Reaction notes

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