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

Participants

Role	Name	HCID	Charge
Reactant	N-Tosylindole	HCID 10956616	—
Reactant	4,4-dimethoxy-4H-naphthalen-1-one	HCID 11095717	—
Product	4-hydroxy 4-[1-(toluene-4-sulfonyl)-1H-indol-2-yl]-4H-naphthalen-1-one	HCID 10387927	23%

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07307099B2
Source dataset	uspto-grants-2007_12
ORD ID	ord-061eebbb581e480ab447efd139852525
Source note	uspto-grants-2007_12