Iodoethane → HCID 118021567, compound

HRID 518327Notes

Reaction equation

HRID 518327 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[H-].[Na+].I[CH2:21][CH3:22]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:10]([CH2:21][CH3:22])[C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 118022092HCID 118022092, compound

Product 1

HCID 118021567HCID 118021567, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the title compound from Example 110, step 1 (150.0 mg, crude) in DMF (10 mL) was added NaH (60.0 mg, 1.5 mmol, 60% in oil) in portions at 0° C. and stirred for 30 min. Then iodoethane (234.0 mg, 1.5 mmol) was added dropwise at 0° C. The reaction mixture was stirred for 2 h at 30° C. It was then quenched with saturated aqueous NH4Cl (15 mL), extracted with ethyl acetate (20 mL), washed with brine (20 mL), dried over Na2SO4, filtered and concentrated to give the title compound (120.0 mg, crude) as a light green solid which was carried forward without purification.

Workup

  1. stirringThe reaction mixture was stirred for 2 h at 30° C
  2. customIt was then quenched with saturated aqueous NH4Cl (15 mL)
  3. extractionextracted with ethyl acetate (20 mL)
  4. washwashed with brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-66fb7b8c9bbc4097b1851e9cf0bab17d
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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