Skatole → HCID 58386489, compound

HRID 74526

Reaction equation

HRID 74526 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[Cl:13][C:14]1[N:19]=[CH:18][N:17]=[C:16]([C:20](Cl)=[O:21])[CH:15]=1.CCOC(C)=O>C1COCC1>[Cl:13][C:14]1[N:19]=[CH:18][N:17]=[C:16]([C:20]([N:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]([CH3:3])=[CH:5]2)=[O:21])[CH:15]=1

Participants

6

Reactant 4

HCID 6736SkatoleHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 184220986-Chloropyrimidine-4-carbonyl chloride

Product 1

HCID 58386489HCID 58386489, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere 120 mg (3.00 mmol) sodium hydride (60% in mineral oil) were added batchwise to 380 mg (2.90 mmol) 3-methylindole in 15 mL THF and the mixture was stirred for 30 min at RT. 500 mg (2.83 mmol) 6-chloropyrimidine-4-carboxylic acid chloride were added batchwise and then the reaction mixture was stirred for 2 h at RT. Then 50 mL EtOAc were added and the mixture was washed with 50 mL saturated sodium hydrogen carbonate solution (1×), 30 mL water and with 50 mL 1 M hydrochloric acid. The organic phase was dried on sodium sulphate, filtered and then evaporated down i. vac. The product was used in the next step without further purification.

Workup

  1. stirringthe reaction mixture was stirred for 2 h at RT
  2. washthe mixture was washed with 50 mL saturated sodium hydrogen carbonate solution (1×), 30 mL water and with 50 mL 1 M hydrochloric acid
  3. customThe organic phase was dried on sodium sulphate
  4. filtrationfiltered
  5. customevaporated down i
  6. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-d1f7ccbf2f7d40a5bcc870d4b8890987
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

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