Isopropyl iodide → HCID 86723686, compound

HRID 577449Notes

Reaction equation

HRID 577449 reaction equation
[Cl:1][C:2]1[C:3]([OH:14])=[C:4]([F:13])[CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[NH:9][CH2:8][CH2:7]2.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:21](I)([CH3:23])[CH3:22]>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:3]([O:14][CH:21]([CH3:23])[CH3:22])=[C:4]([F:13])[CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[NH:9][CH2:8][CH2:7]2

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 86723687HCID 86723687, compound

Product 1

HCID 86723686HCID 86723686, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-chloro-6-fluoro-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one (Cpd O, 131 mg, 0.607 mmol) in DMF (3.0 mL) was added cesium carbonate (0.210 g, 0.645 mmol) and iso-propyl iodide (0.0850 mL, 0.850 mmol). The reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was diluted with EtOAc and washed with water (2×) and brine. The organic layer was concentrated under vacuum and the residue was purified by column chromatography (40-100% EtOAc/heptane) to give the title compound (Cpd P, 62 mg, 40%) as a white solid. MS 258 [M+H].

Workup

  1. washwashed with water (2×) and brine
  2. concentrationThe organic layer was concentrated under vacuum
  3. customthe residue was purified by column chromatography (40-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-4515c48240b941ca8cc45cee9acf848c
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

Loading…