1,2-Dibromoethane → HCID 59216374, compound

HRID 2069809Notes

Reaction equation

HRID 2069809 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:25]=[CH:24][C:8]([CH2:9][N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH2:20][C:21]#[N:22])[CH:16]=3)[C:11]2=[O:23])=[CH:7][CH:6]=1.Br[CH2:27][CH2:28]Br>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:25]=[CH:24][C:8]([CH2:9][N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:20]4([C:21]#[N:22])[CH2:28][CH2:27]4)[CH:16]=3)[C:11]2=[O:23])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydride2×HCID 59216379HCID 59216379, compound

Product 1

HCID 59216374HCID 59216374, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 228 mg of 60% sodium hydride in 15 ml DMF was added 1.2 g of [2-(4-Methoxy-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl]-acetonitrile and after stirring for 15 minutes at room temperature 1.1 g of 1,2-dibromo-ethane in 1.5 ml DMF was added. The resulting mixture was stirred 0.5 hour at room temperature and then more sodium hydride (0.114 g, 2.86 mmole) was added and the reaction mixture was heated for about 10 minutes at 30-35° C. After cooling, the mixture was partitioned between ethyl acetate and brine and the organic layer was dried over sodium acetate and concentrated in vacuo. Purification by silica gel column chromatography with 30%-50% ethylacetate in hexane afforded 1 g of 1-[2-(4-Methoxy-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl]-cyclopropanecarbonitrile.

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was heated for about 10 minutes at 30-35° C
  3. temperatureAfter cooling
  4. customthe mixture was partitioned between ethyl acetate and brine
  5. dry with materialthe organic layer was dried over sodium acetate
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel column chromatography with 30%-50% ethylacetate in hexane

Sources & evidence

ORD record
ord-a924d5062c2e47cfa3adb9996e49b4a8
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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