Indole → 3-iodo-1H-indole

HRID 733038Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.N1C2C(=CC=CC=2)C=N1.[I:19]I>>[I:19][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

Reactant 3

HCID 798Indole

HCID 807Iodine

HCID 92211H-Indazole

Product 1

HCID 112072533-iodo-1H-indole

Procedure

Compounds of formula VIII may also be prepared directly from an indole or indazole of formula XVII by reacting the formula XVII substrate with iodine to give the 3-iodoindole or -indazole of formula XVIII; coupling the formula XVIII compound with an appropriate thiol of formula XIX to give the 3-thioindole or -indazole of formula XX and oxidizing said formula XX compound with a conventional oxidizing agent such as H2O2, m-chloroperbenzoic acid, or the like to afford the desired formula VIII intermediate. The reaction is shown in flow diagram IV.

Sources & evidence

ORD record: ord-129cd3ecfc164df895fd88719d410f83
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589108B2

Reaction notes

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