Ethanol → HCID 59003130, compound

HRID 2353922Notes

Reaction equation

HRID 2353922 reaction equation
C(O)C.[NH2:4][C:5]1C=[C:12]([F:14])[C:11]([CH3:15])=[CH:10][C:6]=1C(O)=O.C[Si](C=[N+]=[N-])(C)C.[CH2:23]([O:25][C:26](=[O:28])[CH3:27])C>>[CH3:23][O:25][C:26](=[O:28])[C:27]1[C:5]([NH2:4])=[CH:6][CH:10]=[C:11]([CH3:15])[C:12]=1[F:14]

Participants

5

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 167693TrimethylsilyldiazomethaneHCID 686786072-Amino-4-fluoro-5-methylbenzoic acid

Product 1

HCID 59003130HCID 59003130, compound

Procedure

Dissolve in ethylacetate (1 mL) and ethanol (1 mL) 6-Amino-2-fluoro-3-methyl-benzoic acid and 2-Amino-4-fluoro-5-methyl-benzoic acid (240 mg, 1.42 mmol) and add (trimethylsilyl) diazomethane (0.7 mL, 1.4 mmol, 2M in hexane) at room temperature and stir the solution for 16 h. Remove the solvent under reduced pressure. Chromatograph the residue over silica gel, eluting with hexanes/ethyl acetate (10:1), to afford the titled compound (50 mg). 1H NMR (CDCl3, 300 MHz) δ 2.13 (d, J=2.4 Hz, 3H), 3.9 (s, 3H), 6.39 (dd, J=0.8, 8.5 Hz, 1H), 7.04 (t, J=8.1 Hz, 1H). MS (ES+): 184 (M+H).

Workup

  1. customRemove the solvent under reduced pressure
  2. washChromatograph the residue over silica gel, eluting with hexanes/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-f4824657f5004d058b9ea56b070b0334
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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