Pyridine → N-methoxy-1-(4-methoxybenzyl)-3-methyl-N-methyl-1H-indole-6-carboxamide

HRID 392197Notes

Reaction equation

HRID 392197 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17](Cl)=[O:18])[CH:15]=3)[C:10]([CH3:20])=[CH:9]2)=[CH:5][CH:4]=1.Cl.[CH3:24][NH:25][O:26][CH3:27].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:27][O:26][N:25]([CH3:24])[C:17]([C:14]1[CH:15]=[C:16]2[C:11]([C:10]([CH3:20])=[CH:9][N:8]2[CH2:7][C:6]2[CH:21]=[CH:22][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:12][CH:13]=1)=[O:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 226634601-(4-methoxybenzyl)-3-methyl-1H-indole-6-carbonyl chloride

Product 1

HCID 22663398N-methoxy-1-(4-methoxybenzyl)-3-methyl-N-methyl-1H-indole-6-carboxamideYield 92.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred solution of 1-(4-methoxybenzyl)-3-methyl-1H-indole-6-carbonyl chloride [2.8 g, Reference Example 42(b)] in chloroform (90 ml) at 0° C. was treated with N,O-dimethylhydroxylamine hydrochloride (0.982 g) and pyridine (1.55 ml). The solution was stirred at room temperature for 1 hour then evaporated. The residue was partitioned between dichloromethane (100 ml) and brine (50 ml). The organic layer was dried over sodium sulphate then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:2, v/v) to yield the title compound (2.8 g).

Workup

  1. customthen evaporated
  2. customThe residue was partitioned between dichloromethane (100 ml) and brine (50 ml)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customthen evaporated
  5. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:2

Sources & evidence

ORD record
ord-40144f501b8f4dd9ab7889bda58e9d68
Source dataset
uspto-grants-2004_10
Patent number
US06800645B1

Reaction notes

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