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

HRID 1903112Notes

Reaction equation

HRID 1903112 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-4fbc0facc1c142b58a312c27b35df4b7
Source dataset
uspto-grants-1984_03
Patent number
US04435403

Reaction notes

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