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

HRID 33576

反応式

HRID 33576 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
180 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-82babac5748d4d23880cd6ea35080aee
出典データセット
uspto-grants-2008_09
特許番号
US07429607B2

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