N-Tosylindole → 4-hydroxy 4-[1-(toluene-4-sulfonyl)-1H-indol-2-yl]-4H-naphthalen-1-one

HRID 969610Notes

Reaction equation

HRID 969610 reaction equation
CO[C:3]1([O:14]C)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[CH:5]=[CH:4]1.[C:16]1([CH3:34])[CH:21]=[CH:20][C:19]([S:22]([N:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=[CH:26]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1>>[OH:14][C:3]1([C:26]2[N:25]([S:22]([C:19]3[CH:20]=[CH:21][C:16]([CH3:34])=[CH:17][CH:18]=3)(=[O:24])=[O:23])[C:33]3[C:28]([CH:27]=2)=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[CH:5]=[CH:4]1

Participants

3

Reactant 2

HCID 10956616N-TosylindoleHCID 110957174,4-dimethoxy-4H-naphthalen-1-one

Product 1

HCID 103879274-hydroxy 4-[1-(toluene-4-sulfonyl)-1H-indol-2-yl]-4H-naphthalen-1-oneYield 23%

Procedure

The title compound was prepared from 4,4-dimethoxy-4H-naphthalen-1-one and 1-(toluene4-sulfonyl)-1H-indole, according to Method E, described above. Yield 23%; mp 110-112° C.; 1H NMR (CDCl3) δ 8.35-8.39 (dd, J=8 Hz, 1H), 8.04 (d, J=8 Hz,1H), 7.74-7.97 (m, 6H), 7.32-7.48 (m, 6H), 6.53 (d, J=10 Hz,1H), 2.52 (s, 3H); 13C NMR (CDCl3) δ 189.7, 154.0, 150.2, 149.8, 148.8, 143.6, 140.1, 137.9, 135.7, 134.8, 133.6, 132.3, 131.7, 131.3, 130.7, 129.3, 126.6, 120.4, 120.3, 74.8, 26.6; MS (AP+) m/z 430.09 (M++1), 412.14.

Sources & evidence

ORD record
ord-061eebbb581e480ab447efd139852525
Source dataset
uspto-grants-2007_12
Patent number
US07307099B2

Reaction notes

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