3-(Trifluoromethyl)phenyl isocyanate → HCID 59427911, compound

HRID 1042725Notes

Reaction equation

HRID 1042725 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 59427911HCID 59427911, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3cefa9eaeb4846d79339fbd6ed66354e
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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