Water → HCID 66819254, compound

HRID 2045963Notes

Reaction equation

HRID 2045963 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1.[C:21]([O:25][C:26](=[O:31])[NH:27][CH2:28][CH2:29]Br)([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C(=O)C>[C:21]([O:25][C:26](=[O:31])[NH:27][CH2:28][CH2:29][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 44315704HCID 44315704, compound

Product 1

HCID 66819254HCID 66819254, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 3.79 g (14.19 mmol) of 4-hydroxy-3-(3-methoxy-phenyl)-2H-isoquinolin-1-one in N,N-dimethylacetamide (90 mL), 3.18 g (14.19 mmol) of (2-bromo-ethyl)-carbamic acid tert-butyl ester and 5.09 g (15.6 mmol) of cesium carbonate were added and the resulting mixture was stirred at room temperature for 2 hours under argon. Water was added to the reaction mixture and this was extracted twice with ethyl acetate. The combined organic layers were washed at least three times with water and then evaporated to dryness. The crude was purified by flash chromatography (eluant: ethyl acetate/hexane 1/1) to afford 3.2 g of the title compound (55%).

Workup

  1. extractionthis was extracted twice with ethyl acetate
  2. washThe combined organic layers were washed at least three times with water
  3. customevaporated to dryness
  4. customThe crude was purified by flash chromatography (eluant: ethyl acetate/hexane 1/1)

Sources & evidence

ORD record
ord-f416acc489834c3f9329587a92aed658
Source dataset
uspto-grants-2013_11
Patent number
US08592416B2

Reaction notes

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