Ethyl bromoacetate → ethyl[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]acetate

HRID 2059940Notes

Reaction equation

HRID 2059940 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[C:25]([CH3:34])=[C:26]4[C:31](=[CH:32][CH:33]=3)[CH2:30][NH:29][CH2:28][CH2:27]4)[N:20]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44]>CN(C=O)C.C(OCC)(=O)C>[CH2:46]([O:45][C:43](=[O:44])[CH2:42][N:29]1[CH2:28][CH2:27][C:26]2[C:31](=[CH:32][CH:33]=[C:24]([C:21]3[N:20]=[C:19]([C:11]4[CH:12]=[CH:13][C:14]([O:15][CH:16]([CH3:18])[CH3:17])=[C:9]([Cl:8])[CH:10]=4)[O:23][N:22]=3)[C:25]=2[CH3:34])[CH2:30]1)[CH3:47]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 684983726-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-1,2,3,4-tetrahydroisoquinoline trifluoroacetate

Product 1

HCID 59370488ethyl[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]acetateYield 88.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-1,2,3,4-tetrahydroisoquinoline trifluoroacetate (Example 10; 90 mg; 0.18 mmol) in DMF (3 ml) under nitrogen at room temperature was added caesium carbonate (177 mg; 0.54 mmol) followed by ethyl bromoacetate (0.026 ml; 0.23 mmol). After 35 min, the mixture was diluted with ethyl acetate and the precipitate removed. The solution was washed with water and the aqueous layer further extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo to give the title compound (75 mg).

Workup

  1. customthe precipitate removed
  2. washThe solution was washed with water
  3. extractionthe aqueous layer further extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4468da62fab41d691016216164c0500
Source dataset
uspto-grants-2012_10
Patent number
US08278324B2

Reaction notes

Loading…