1-Naphthaleneboronic acid → 5-Methyl-4-naphthalen-1-yl-oxazol-2-ylamine

HRID 33576

Reaction equation

HRID 33576 reaction equation
C(OC([NH:8][C:9]1[O:10][C:11]([CH3:22])=[C:12](OS(C(F)(F)F)(=O)=O)[N:13]=1)=O)(C)(C)C.[C:23]1(B(O)O)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.C([O-])(=O)C.[K+]>O1CCOCC1>[CH3:22][C:11]1[O:10][C:9]([NH2:8])=[N:13][C:12]=1[C:31]1[C:32]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 2545321-Naphthaleneboronic acidHCID 517044Potassium AcetateHCID 86590770Trifluoro-methanesulfonic acid 2-tert-butoxycarbonylamino-5-methyl-oxazol-4-yl ester

Product 1

HCID 597968265-Methyl-4-naphthalen-1-yl-oxazol-2-ylamineYield 14%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of trifluoro-methanesulfonic acid 2-tert-butoxycarbonylamino-5-methyl-oxazol-4-yl ester (100 mg), 1-naphthaleneboronic acid (61 mg) palladium (0) tetrakis(triphenylphosphine) (17 mg), potassium acetate (85 mg) and 1,4-dioxane (5 mL) was heated at 180° C. for 24 hours. The solvent was removed under reduced pressure and to the resulting yellow oil was added dichloromethane (18 mL) and trifluoroacetic acid (2 mL). The mixture was stirred at room temperature for 1 hour and then the solvent was removed under reduced pressure, the resulting oil was diluted with ethyl acetate and washed with a saturated solution of sodium hydrogen carbonate, brine, dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to afford a brown oil. Purification by column chromatography afforded 5-methyl-4-naphthalen-1-yl-oxazol-2-ylamine (30) (9 mg, 14%) as a white solid. 1H NMR (DMSO-D6): 2.15 (3H, s), 6.5 (2H, br s), 7.4-7.5 (4H, m), 7.85-7.90 (2H, m), 8.2 (1H, m). Mass Spectrum (m/z): 225 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure and to the resulting yellow oil
  2. additionwas added dichloromethane (18 mL) and trifluoroacetic acid (2 mL)
  3. customthe solvent was removed under reduced pressure
  4. additionthe resulting oil was diluted with ethyl acetate
  5. washwashed with a saturated solution of sodium hydrogen carbonate, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. customto afford a brown oil
  10. customPurification by column chromatography

Sources & evidence

ORD record
ord-82babac5748d4d23880cd6ea35080aee
Source dataset
uspto-grants-2008_09
Patent number
US07429607B2

Linked notes

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