Triethylamine → HCID 19016497, compound

HRID 1728600Notes

Reaction equation

HRID 1728600 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH3:21])[CH:16]=[CH:15]2.C(N(CC)CC)C>O1CCCC1>[CH3:21][N:17]1[C:18]2[C:14](=[CH:13][C:12]([NH:11][C:2](=[O:3])[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:20][CH:19]=2)[CH:15]=[CH:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 27695641-methyl-1H-indol-5-amine

Product 1

HCID 19016497HCID 19016497, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of phenyl chloroformate (2.21 ml; 17.4 mM) in dry tetrahydrofuran (30 ml), cooled in a carbon tetrachloride/solid carbon dioxide bath, was added 5-amino-1-methylindole (D3) (2.31 g; 15.8 mM) followed by triethylamine (2.40 ml; 17.4 mM). The mixture was stirred for 45 min at -20° C. (bath temp.), then evaporated and the residue was dissolved in ethyl acetate, washed with brine, dried and evaporated to give the title compound (4.29 g; 100%), m.p. 103°-107° C. (EtOAc/petrol).

Workup

  1. customevaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-a60ed79f6a584f81a704d4ee4d7acb0f
Source dataset
uspto-grants-1994_07
Patent number
US05328922

Reaction notes

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