Ethyl Bromide → HCID 25061301, compound

HRID 1673213Notes

Reaction equation

HRID 1673213 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[CH:25]([OH:26])[CH2:24][C:23]([CH3:28])([CH3:27])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.Br[CH2:30][CH3:31].[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[CH:25]([O:26][CH2:30][CH3:31])[CH2:24][C:23]([CH3:28])([CH3:27])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 25061041HCID 25061041, compound

Product 1

HCID 25061301HCID 25061301, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the product of Example 68 (60 mg, 0.14 mmol) in DMF (1 mL) was added bromoethane (152 mg, 1.4 mmol) and NaH (6 mg, 0.14 mmol) and the suspension was stirred for 1 h at rt. The reaction was quenched by adding 1N HCl and water. The reaction was diluted with EtOAc, washed with a saturated aq NaHCO3 solution, brine, dried (Na2SO4), filtered and concentrated The residue was purified by flash chromatography on silica gel gradient eluted with 85% CH2Cl2 in hexane to afford the title compound. (LC-2) HPLC/MS: 462.2 (M+1), 464.2 (M+3); Rt=4.51 min

Workup

  1. customThe reaction was quenched
  2. additionby adding 1N HCl and water
  3. additionThe reaction was diluted with EtOAc
  4. washwashed with a saturated aq NaHCO3 solution, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated The residue
  8. customwas purified by flash chromatography on silica gel gradient
  9. washeluted with 85% CH2Cl2 in hexane

Sources & evidence

ORD record
ord-c03f6b6c2d564178bdcf310cfdd4047d
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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