7-Hydroxynaphthalene-2-sulfonamide → 7-(2-(tert-Butyldimethylsilyloxy)ethoxy)naphthalene-2-sulfonamide

HRID 528816Notes

Reaction equation

HRID 528816 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>>[Si:20]([O:19][CH2:18][CH2:17][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([S:12]([NH2:15])(=[O:13])=[O:14])=[CH:9]2)=[CH:4][CH:3]=1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

3

Reactant 2

HCID 7518327-Hydroxynaphthalene-2-sulfonamideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 710623897-(2-(tert-Butyldimethylsilyloxy)ethoxy)naphthalene-2-sulfonamideYield 48%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 17, 7-hydroxynaphthalene-2-sulfonamide (40 mg, 0.18 mmol) and (2-bromoethoxy)(tert-butyl)dimethylsilane (43 mg, 0.18 mmol) were converted to the title compound (33 mg, 48%) after purification using flash column chromatography (gradient from 0% to 2% MeOH/CH2Cl2). 1H NMR (CDCl3) δ 8.31 (s, 1H), 7.84-7.82 (m, 1H), 7.77-7.73 (m, 2H), 7.26 (dd, J=8.9, 2.5 Hz, 1H), 7.19 (d, J=2.2 Hz, 1H), 4.13 (t, J=4.9 Hz, 2H), 4.02 (t, J=4.9 Hz, 2H), 0.90 (s, 9H), 0.10 (s, 6H); MS(ESI−) m/z 380.4 (M−H)−.

Sources & evidence

ORD record
ord-ad02fac4e76a436980584a04711df54d
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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