Cesium carbonate → 6-Bromo-2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)isoquinolin-1(2H)-one

HRID 906419Notes

Reaction equation

HRID 906419 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][C:9]([CH3:20])([CH3:19])[CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[Br:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[C:28](=[O:32])[NH:27][CH:26]=[CH:25]2>CN(C=O)C.O>[Br:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[C:28](=[O:32])[N:27]([CH2:8][C:9]([CH3:20])([CH3:19])[CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:26]=[CH:25]2

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11780954(3-Bromo-2,2-dimethylpropoxy)(tert-butyl)dimethylsilaneHCID 158851826-Bromoisoquinolin-1(2H)-one

Product 1

HCID 671303156-Bromo-2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)isoquinolin-1(2H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (53.3 g) and (3-bromo-2,2-dimethylpropoxy)(tert-butyl)dimethylsilane (27.62 g) were added to a solution of 6-bromoisoquinolin-1(2H)-one (Example 26a, 18.33 g) in DMF (125 mL) with stirring at room temperature under nitrogen. The resulting mixture was stirred at 100° C. for 6 h, diluted with water (300 mL), and extracted with diethyl ether (300 mL×3). The combined organic extracts were dried (MgSO4), filtered and evaporated.

Workup

  1. stirringThe resulting mixture was stirred at 100° C. for 6 h
  2. extractionextracted with diethyl ether (300 mL×3)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-9829003775bf4031b32486508abfa4ca
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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