3-(Trifluoromethyl)phenyl isocyanate → HCID 59427911、化合物

HRID 502769ノート

反応式

HRID 502769 の反応式
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[N:13]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1)=[C:14]=[O:15].[NH4+].[Cl-]>CN(C=O)C>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:14]([NH:13][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=2)=[O:15])[CH:3]=1

参加物

6

反応物 4

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 112072533-iodo-1H-indole

生成物 1

HCID 59427911HCID 59427911、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-iodoindole (583 mg, 2.4 mmol) (Witulski, B.; Buschmann, N.; Bergstrasser, U. Tetrahedron 2000, 56, 8473-8480.) in DMF (10 mL) at 0° C. was added NaH (125 mg, 3.1 mmol, 60% dispersion in mineral oil). The reaction mixture was allowed to warm to room temperature and stir for 0.5 h. Then 1-isocyanato-3-(trifluoromethyl)benzene (0.38 mL, 2.64 mmol) was added and allowed to stir for an additional 0.5 h. Sat. aq. NH4Cl (20 mL) was added and the mixture was poured onto water (50 mL). The aqueous layer was extracted with Et2O (3×25 mL). The combined organics were washed with brine (10 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude concentrate was purified via automated flash chromatography (silica gel, 0 to 50% EtOAc in hexanes, gradient elution) to afford 3-iodo-N-(3-(trifluoromethyl)phenyl)-1H-indole-1-carboxamide.

後処理

  1. stirringto stir for an additional 0.5 h
  2. additionthe mixture was poured onto water (50 mL)
  3. extractionThe aqueous layer was extracted with Et2O (3×25 mL)
  4. washThe combined organics were washed with brine (10 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. concentrationThe crude concentrate
  9. customwas purified
  10. washflash chromatography (silica gel, 0 to 50% EtOAc in hexanes, gradient elution)

出典と根拠

ORDレコード
ord-5d746a577c354362955b7de12e64b098
出典データセット
uspto-grants-2010_08
特許番号
US07776869B2

反応ノート

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