4-Bromobenzenesulfonamide → HCID 16110647, compound

HRID 605625Notes

Reaction equation

[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([S:33]([NH2:36])(=[O:35])=[O:34])=[CH:29][CH:28]=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=CC(S(N)(=O)=O)=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:32]=[CH:31][C:30]([S:33]([NH2:36])(=[O:35])=[O:34])=[CH:29][CH:28]=3)=[CH:25][N:26]=2)=[O:8])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Reactant 3

HCID 696964-Bromobenzenesulfonamide

HCID 16110680HCID 16110680, compound

HCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110647HCID 16110647, compoundYield 82%

Procedure

4-(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 (63 mg, 0.095 mmol) and 4-bromobenzenesulfonamide following General Procedure A. Flash chromatography (2-20% EtOAc/hexanes) yielded the title compound as a white solid (41 mg, 82%): 1H NMR (CDCl3, 500 MHz) δ 8.05 (d, 2H, J=8.5 Hz), 7.83 (d, 2H, J=8.5 Hz), 7.49 (s, 1H), 7.36-7.32 (m, 2H), 7.25-7.22 (m, 3H), 5.39 (s, 2H), 4.92 (t, 1H, J=6.0 Hz), 2.67 (t, 2H, J=7.5 Hz), 2.03-1.96 (m, 2H), 1.74-1.67 (m, 2H), 1.46-1.38 (m, 6H), 0.97 (s, 9H), 0.18 (s, 3H), 0.07 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 166.6, 149.9, 141.7, 132.8, 129.6, 128.8, 128.7, 128.4, 127.6, 126.0, 124.9, 124.5, 69.1, 36.8, 36.3, 31.8, 29.6, 26.1, 26.1, 25.5, 18.6, −4.5, −4.6.

Sources & evidence

ORD record: ord-6c2fedddbc014e459873f74f86095686
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915270B2

Reaction notes

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