4-Toluenesulfonyl chloride → 5-fluoro-N-tosylindole

HRID 969603Notes

Reaction equation

HRID 969603 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.[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[CH:16]2>>[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[CH:17]=[CH:16]2

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 678615-Fluoroindole

Product 1

HCID 167513275-fluoro-N-tosylindoleYield 100%

Procedure

The title compound was prepared from toluene-4-sulfonyl chloride and 5-fluoro-1H-indole, according to Method A, described above. Yield 100%; mp 106-108° C.; 1H NMR (CDCl3) δ 8.13-8.19 (dd, J=4, 8 Hz, 1H), 7.96 (d, J=8 Hz, 2H), 7.82 (d, J=4 Hz, 1H), 7.40-7.48 (m, 3H), 7.25-77.38 (m,1H), 6.83 (d, J=4 Hz, 1H), 2.55 (s, 3H); 13C NMR (CDCl3) δ 161.9, 158.1, 145.6, 135.4, 132.2, 132.1, 131.6, 130.3, 128.5, 127.2, 115.0, 114.9, 113.2, 112.8, 109.4, 109.3, 107.5, 107.1, 21.9.

Sources & evidence

ORD record
ord-c90672db8ebb4e959e2a4821221e9934
Source dataset
uspto-grants-2007_12
Patent number
US07307099B2

Reaction notes

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