Phosgene → HCID 19016507, compound

HRID 1728603Notes

Reaction equation

HRID 1728603 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([CH3:12])=[C:5]2[CH2:13][CH3:14].[C:15](Cl)([Cl:17])=[O:16].C(N(CC)CC)C.[NH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1>ClCCl.C1(C)C=CC=CC=1.[OH-].[Na+].O>[ClH:17].[CH3:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][C:15]([NH:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[O:16])=[CH:10][CH:9]=2)[C:5]([CH2:13][CH3:14])=[C:6]1[CH3:12]

Participants

9

Reactant 4

HCID 6371PhosgeneHCID 8471TriethylamineHCID 100093-AminopyridineHCID 19016521HCID 19016521, compound

Product 1

HCID 19016507HCID 19016507, compoundYield 17%

Reagents, catalysts & solvents 4

HCID 14798Sodium HydroxideCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the aminoindole (D1) (0.71 g; 3.78 mM) in dichloromethane (13.5 ml) at 0° C. was added a 12.5% solution of phosgene in toluene (3.28 ml; 3.79 mM). After stirring for 0.5 h, triethylamine (1.15 ml ) was added and stirring was continued for 0.5 h. A solution of 3-aminopyridine (0.34 g; 3.6 mM) in dichloromethane (10 ml) was then added, and stirring continued for 3.5 h at room temperature. Several drops of aqueous sodium hydroxide were added to the reaction mixture which was vigorously stirred for 0.5 h. The reaction mixture was diluted with water and extracted with dichloromethane. The combined organic extracts were washed with brine, dried over sodium sulphate and evaporated to dryness. Chromatography on silica using dichloromethane as eluant afforded the title compound (0.2 g; 17%) which was converted to the hydrochloride salt using hydrogen chloride in ether/ethanol, m.p. 158°-165° C.

Workup

  1. stirringstirring
  2. waitwas continued for 0.5 h
  3. stirringstirring
  4. waitcontinued for 3.5 h at room temperature
  5. stirringwas vigorously stirred for 0.5 h
  6. extractionextracted with dichloromethane
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over sodium sulphate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-509da71529584e15971d5fa84877a7f6
Source dataset
uspto-grants-1994_07
Patent number
US05328922

Reaction notes

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