5-Fluoro-6-methylthioindole-2,3-dione → 5-Fluoro-6-methylthioindole

HRID 844208Notes

Reaction equation

HRID 844208 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[S:11][CH3:12])[NH:7][C:6](=O)[C:5]2=O.ClC1C=C(F)C=C2C=1NC=C2>>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[S:11][CH3:12])[NH:7][CH:6]=[CH:5]2

Participants

3

Reactant 2

HCID 226127305-Fluoro-6-methylthioindole-2,3-dioneHCID 226127407-chloro-5-fluoro-1H-indole

Product 1

HCID 226127025-Fluoro-6-methylthioindole

Procedure

5-Fluoro-6-methylthioindole was prepared from 5-fluoro-6-methylthioindole-2,3-dione according to the method described in the preparation of 7-chloro-5-fluoroindole as a white solid (1.21 g, 37%): mp 51° C.; C9H8FNS requires: C, 59.65; H, 4.45; N, 7.73; S, 17.69%. Found C, 59.75; H, 4.44; N, 7.72; S, 17.65%; IR δmax (Nujol)/cm−1 3461, 3408, 3361, 2925, 2855, 1455, 1304 and 1137; NMR δH (400 MHz, CDCl3) 2.49 (3H, s), 6.49-6.51 (1H, m), 7.22 (1H, t, J 3.0 Hz), 7.30 (1H, d, J 10.0 Hz), 7.36 (1H, d, J 6.5 Hz), 8.0-8.25 (1H, brm).

Sources & evidence

ORD record
ord-86c99572b5df4a499b5d4e78c17118ce
Source dataset
uspto-grants-2002_04
Patent number
US06380238B1

Reaction notes

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