1,2-Dibromoethane → HCID 57524148, compound

HRID 1477878Notes

Reaction equation

HRID 1477878 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17]2)([CH2:14][CH3:15])[C:9](=[O:13])[CH2:10][C:11]#[N:12])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:33][CH2:34]Br>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][S:26]([CH3:29])(=[O:27])=[O:28])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17]2)([C:9]2[O:13][CH2:33][CH2:34][C:10]=2[C:11]#[N:12])[CH2:14][CH3:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 57524147HCID 57524147, compound

Product 1

HCID 57524148HCID 57524148, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(1-(3-(4-chlorophenyl)-1-cyano-2-oxopentan-3-yl)-1H-indol-4-yl)methanesulfonamide (50 mg, 0.116 mmol, enantiomer A), as described in Example 28 step A, in DMF (2 mL) was added NaH (9 mg, 0348 mmol, 60% in oil) at 0° C. After stirring for 30 min, 1,2-dibromoethane (22 mg, 0.116 mmol) was added to the mixture at 0° C. The resulting mixture was stirred at 0° C. for another 1 h, and then quenched with water (15 mL), extracted with ethyl acetate. The combined organic layers were washed with brine (10 mL), dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography eluting with PE/EA (5/1 to 3/1, v/v) to give the title compound as a colorless amorphous solid. LC/MS m/z=456.1[M+H]+.

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for another 1 h
  2. customquenched with water (15 mL)
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with PE/EA (5/1 to 3/1

Sources & evidence

ORD record
ord-58b6277a174d4068a2d14a4bf0199912
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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