Sodium hydride → HCID 68679962, compound

HRID 2353954Notes

Reaction equation

HRID 2353954 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[NH:11][C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13].[H-].[Na+].Br[CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[N:11]([CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:12]([O:14][CH:15]([CH3:16])[CH3:17])=[O:13]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 68681493HCID 68681493, compound

Product 1

HCID 68679962HCID 68679962, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Add a solution of 2-Isopropoxycarbonylamino-6-fluor-benzoic acid methyl ester (3.0 g, 11.76 mmol) in DMF (43 mL) to a suspension of sodium hydride 60% dispersion mineral oil (471 mg, 11.76 mmol) in DMF (43 mL) at 0° C. under an atmosphere of nitrogen and allow to reach room temperature over 1 h. Add ethyl 4-bromobutyrate (2.5 mL, 17.64 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 title compound (2.96, 68%). MS (ES+): 370 (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-d6f7214bd0b94311aeb49a9e4fc5506a
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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