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

HRID 33576

반응식

HRID 33576 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
180 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-82babac5748d4d23880cd6ea35080aee
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429607B2

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