Methyl chloroformate → N-(1-Methyl-1H-indol-5-yl)-N-(4-pyridinyl) carbamic acid methyl ester

HRID 21559

Reaction equation

HRID 21559 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][C:12]([NH:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[CH:13][CH:14]=2)[CH:9]=[CH:8]1>C(Cl)Cl.C(N(CC)CC)C>[CH3:5][O:4][C:2](=[O:3])[N:16]([C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([CH3:6])[CH:8]=[CH:9]2)[C:17]1[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 98159221-Methyl-5-(4-pyridinylamino)-1H-indole

Product 1

HCID 15291817N-(1-Methyl-1H-indol-5-yl)-N-(4-pyridinyl) carbamic acid methyl esterYield 98.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of methyl chloroformate (1.3 g) in 5 ml DCM was added to a solution of 1-methyl-5-(4-pyridinylamino)-1H-indole (2.5 g) in 120 ml DCM and 6 ml triethylamine (4.4 g). After stirring one hour at ambient temperature the reaction mixture was washed with water and saturated sodium chloride, dried (anhydrous magnesium sulfate), filtered and evaporated to 4 g of a solid. Elution through silica with 50% ethyl acetate in dichloromethane via flash column chromatography yielded 3.1 g of a solid. Recrystallization from methanol yielded 2.4 g of crystals, mp 157°-159° C.

Workup

  1. washwas washed with water and saturated sodium chloride
  2. dry with materialdried (anhydrous magnesium sulfate)
  3. filtrationfiltered
  4. customevaporated to 4 g of a solid
  5. washElution through silica with 50% ethyl acetate in dichloromethane via flash column chromatography

Sources & evidence

ORD record
ord-13377cdf490c4bb79b6f3cd315fa58ef
Source dataset
uspto-grants-1995_06
Patent number
US05424322

Linked notes

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