Sodium hydride → HCID 68681230, compound

HRID 2353947Notes

Reaction equation

HRID 2353947 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([CH3:11])[C:5]=1[NH:12][C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14].[H-].[Na+].Br[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([CH3:11])[C:5]=1[N:12]([CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:13]([O:15][CH:16]([CH3:17])[CH3:18])=[O:14]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 68679050Methyl 4-bromo-3-methyl-2-[[(1-methylethoxy)carbonyl]amino]benzoate

Product 1

HCID 68681230HCID 68681230, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Add a solution of 2-Isopropoxycarbonylamino-4-bromo-3-methyl-benzoic acid methyl ester (3.36 g, 10.18 mmol) in DMF (37 mL) to a suspension of sodium hydride 60% dispersion mineral oil (407 mg, 10.18 mmol) in DMF (37 mL) at 0° C. under an atmosphere of nitrogen and allow to reach room temperature over 1 h. Add ethyl 4-bromobutyrate (2.2 mL, 15.27 mmol) and stir at room temperature for 14 h. Dilute with ethyl acetate, wash with 1M HCl, water and brine. Dry the organic layer over anhydrous magnesium sulfate, filter and remove the solvent under reduced pressure. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate, to provide the titled compound (3.47 g, 77%): MS (ES+): 445 (M+H).

Workup

  1. washwash with 1M HCl, water and brine
  2. dry with materialDry the organic layer over anhydrous magnesium sulfate
  3. filtrationfilter
  4. customremove the solvent under reduced pressure
  5. customPurify the residue by flash chromatography
  6. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-e61dec3c8eb94bf4b000dd9bbd1d7d35
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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