Sodium Methoxide → HCID 57744887, compound

HRID 1661493Notes

Reaction equation

HRID 1661493 reaction equation
BrC1SC([C:7]([O:9][CH3:10])=[O:8])=C(NC)C=1C.[CH3:14][O-].[Na+].[Br:17][C:18]1[S:22][C:21]([C:23]([O:25]C)=O)=[C:20]([N:27]([CH3:34])[C:28](=[O:33])[C:29](F)(F)F)[C:19]=1[CH3:35]>CO>[Br:17][C:18]1[S:22][C:21]2[C:23]([OH:25])=[C:29]([C:7]([O:9][CH2:10][CH3:14])=[O:8])[C:28](=[O:33])[N:27]([CH3:34])[C:20]=2[C:19]=1[CH3:35]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 66743799HCID 66743799, compoundHCID 86631544HCID 86631544, compound

Product 1

HCID 57744887HCID 57744887, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-bromo-4-methyl-3-(methylamino)thiophene-2-carboxylate. Sodium methanolate (3.9 mL, 1.9 mmol) was added to a suspension of methyl 5-bromo-4-methyl-3-(2,2,2-trifluoro-N-methylacetamido)thiophene-2-carboxylate (0.70 g, 1.9 mmol) in MeOH (5 mL) and stirred for 1 hour. The solvent was removed, and the residue was dissolved in CHCl3, washed with water, brine, dried over MgSO4, and evaporated. The residue was purified by flash chromatography using EtOAc/hexanes to give the title compound. MS (ESI) m/z: Calculated 264.1; Observed; 265.9. 1H NMR (300 MHz, CDCl3) δ ppm 6.85 (1H, br. s.), 3.79 (3H, s), 3.06 (3H, s), 2.28 (3H, s).

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in CHCl3
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-f904d624e6b74f14901d0168ef73dd23
Source dataset
uspto-grants-2011_10
Patent number
US08030346B2

Reaction notes

Loading…