5-Bromo-2-thiophenesulfonamide → HCID 16110630, compound

HRID 605667Notes

Reaction equation

HRID 605667 reaction equation
[Si:1]([O:8][CH:9]([C:22]1[O:23][C:24]([Sn](CCCC)(CCCC)CCCC)=[CH:25][N:26]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:41]1[S:45][C:44]([S:46]([NH2:49])(=[O:48])=[O:47])=[CH:43][CH:42]=1>>[Si:1]([O:8][CH:9]([C:22]1[O:23][C:24]([C:41]2[S:45][C:44]([S:46]([NH2:49])(=[O:48])=[O:47])=[CH:43][CH:42]=2)=[CH:25][N:26]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 12413045-Bromo-2-thiophenesulfonamideHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110630HCID 16110630, compoundYield 75%

Procedure

The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (54 mg, 0.081 mmol) and 5-bromothiophene-2-sulfonamide following General Procedure A. Flash chromatography (10-20% EtOAc/hexanes) yielded the title compound as a white solid (33 mg, 75%): 1H NMR (CDCl3, 500 MHz) δ 7.68 (d, 1H, J=4.0 Hz), 7.36-7.33 (m, 3H), 7.29 (d, 1H, J=3.5 Hz), 7.26-7.23 (m, 3H), 5.29 (s, 2H), 4.89 (t, 1H, J=6.0 Hz), 2.67 (t, 2H, J=7.5 Hz), 2.02-1.95 (m, 2H), 1.74-1.59 (m, 2H), 1.40-1.38 (m, 6H), 0.97 (s, 9H), 0.17 (s, 3H), 0.08 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 166.2, 145.2, 143.2, 142.5, 136.4, 132.7, 128.8, 128.7, 126.0, 124.2, 123.8, 68.9, 36.7, 36.3, 31.8, 29.6, 26.1, 26.1, 25.5, 18.6, −4.5, −4.7.

Sources & evidence

ORD record
ord-840f7b8400084fed8309fff008fdd3ac
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

Loading…