Indole → N-Tosylindole

HRID 969599Notes

Reaction equation

HRID 969599 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1>>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 798IndoleHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 10956616N-TosylindoleYield 91%

Procedure

The title compound was prepared from toluene-4-sulfonyl chloride and 1H-indole, according to Method A, described above. Yield 91%; mp 60-62° C.; 1H NMR (CDCl3) δ 8.0-8.03 (dd, J=8 Hz, 1H), 7.78 (d, J=7 Hz, 2H), 7.57 (d, J=4 Hz, 1H), 7.52-7.56 (m, 1H), 7.26-7.36 (m, 2H), 7.20-7.23 (d, J=8 Hz, 2H), 6.66-6.68 (dd, J=4 Hz, 1H), 2.30 (s, 3H); 13C NMR (CDCl3) δ 145.4, 135.7, 135.3, 131.2, 130.3, 127.2, 126.8, 124.9, 123.7, 121.8, 113.9, 109.5, 21.9; MS (ES+) m/z 271.93 (M+).

Sources & evidence

ORD record
ord-9150bf18864145a3a285e7d76d6ff6cd
Source dataset
uspto-grants-2007_12
Patent number
US07307099B2

Reaction notes

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