Triethylamine → HCID 86654949, compound

HRID 1615597Notes

Reaction equation

HRID 1615597 reaction equation
[C:1]([O:5][C:6]([C:8]1[N:9]([C:23]2[CH:27]=[CH:26][S:25][CH:24]=2)[C:10]2[C:15]([C:16]=1[NH2:17])=[C:14]([CH3:18])[C:13]([C:19]([F:22])([F:21])[F:20])=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:29](Cl)([O:31]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([C:8]1[N:9]([C:23]2[CH:27]=[CH:26][S:25][CH:24]=2)[C:10]2[C:15]([C:16]=1[N:17]=[C:29]=[O:31])=[C:14]([CH3:18])[C:13]([C:19]([F:21])([F:20])[F:22])=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 68756369HCID 68756369, compound

Product 1

HCID 86654949HCID 86654949, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 3-amino-1-thiophen-3-yl-methyl-5-trifluoromethyl-1H-indole-2-carboxylic acid tert-butyl ester 1E (1.74 g, 4.39 mmol) in anhydrous toluene (50 mL) was added triphosgene (0.44 g, 1.48 mmol) and triethylamine (0.89 g, 8.81 mmol). The reaction mixture was heated at reflux for 3 hours. Toluene (50 mL) was added and the organic layer was washed with water and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure to provide 3-isocyanato-1-thiophen-3-yl-methyl-5-trifluoromethyl-1H-indole-2-carboxylic acid tert-butyl ester 1F which was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. washthe organic layer was washed with water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customThe organic solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c0e8f4666bea4de8a5086b4b84280071
Source dataset
uspto-grants-2014_07
Patent number
US08765757B2

Reaction notes

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