Iodine → Ethyl 6-iodo-4-(methoxymethyl)-9H-pyrido[3,4-b]indole-3-carboxylate

HRID 1982453Notes

Reaction equation

HRID 1982453 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].[I:22]Cl.II>C(Cl)Cl.N1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[CH:15][C:14]([I:22])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 807IodineHCID 24640Iodine chloride2×HCID 13041786HCID 13041786, compound

Product 1

HCID 13041796Ethyl 6-iodo-4-(methoxymethyl)-9H-pyrido[3,4-b]indole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 g of 4-methoxymethyl-beta-carboline-3-carboxylic-acid-ethylester in 20 ml of methylene chloride and 1.5 ml of pyridine is mixed dropwise with 1.5 ml of iodine chloride at room temperature. After 60 minutes, another 1.5 ml of iodine chloride is added and then 200 mg of iodine. The mixture is stirred for another 2 h at room temperature and then poured into an ice-cold saturated sodium thiosulfate solution, followed by extraction with methylene chloride. Crystallization in ethyl acetate yields 520 mg of 6-iodo-4-methoxymethyl-beta-carboline-3-carboxylic-acid-ethylester with a m.p. of 204°-206° C.

Workup

  1. extractionfollowed by extraction with methylene chloride
  2. customCrystallization in ethyl acetate

Sources & evidence

ORD record
ord-bc7fd78e0c724dc4867c6057977011b6
Source dataset
uspto-grants-1986_06
Patent number
US04596808

Reaction notes

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