3-Bromobenzene-1-sulfonamide → 3-(2-(7-Phenylheptanoyl)oxazol-5-yl)benzenesulfonamide

HRID 605624Notes

Reaction equation

HRID 605624 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:28]=[C:29]([S:33]([NH2:36])(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=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(C)(C)C)(C)C.[Si](OC(C1OC([Sn](CCCC)(CCCC)CCCC)=CN=1)CCCCCCC1C=CC=CC=1)(C(C)(C)C)(C)C.BrC1C=C(S(N)(=O)=O)C=CC=1>>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]([C:22]2[O:23][C:24]([C:27]3[CH:28]=[C:29]([S:33]([NH2:36])(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=3)=[CH:25][N:26]=2)=[O:8])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 27347653-Bromobenzene-1-sulfonamideHCID 161106753-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)benzenesulfonamideHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 161107013-(2-(7-Phenylheptanoyl)oxazol-5-yl)benzenesulfonamideYield 91%

Procedure

3-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)benzenesulfonamide. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (75 mg, 0.113 mmol) and 3-bromobenzenesulfonamide following General Procedure A. Flash chromatography (10-30% EtOAc/hexanes) yielded the title compound as a white solid (55 mg, 91%): 1H NMR (CD3OD, 500 MHz) δ 8.24 (m, 1H), 7.92 (d, 1H, J=8.0 Hz), 7.74 (d, 1H, J=8.0 Hz), 7.64 (t, 1H, J=7.6 Hz), 7.58 (s, 1H), 7.24-7.20 (m, 2H), 7.14-7.13 (m, 3H), 4.88 (ex s, 2H), 3.32-3.31 (m, 1H), 2.58 (t, 2H, J=7.6 Hz), 1.98-1.86 (m, 2H), 1.69-1.60 (m, 2H), 1.38-1.34 (m, 6H), 0.90 (s, 9H), 0.12 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 165.9, 150.3, 142.7, 130.7, 128.9, 128.8, 128.6, 128.2, 128.2, 128.0, 125.4, 124.7, 122.3, 36.1, 35.6, 31.4, 28.9, 28.8, 28.0, 25.0, 24.9, 17.8, −6.0, −6.1.

Sources & evidence

ORD record
ord-23dae72e7c2243779838554792083ba4
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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