3-Bromobenzamide → HCID 16110641, compound

HRID 605612Notes

Reaction equation

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

Participants

Reactant 3

HCID 898073-Bromobenzamide

HCID 16110609HCID 16110609, compound

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

Product 1

HCID 16110641HCID 16110641, compoundYield 96%

Procedure

3-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)benzamide. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (72 mg, 0.109 mmol) and 3-bromobenzamide following General Procedure A. Flash chromatography (10-40% EtOAc/hexanes) yielded the title compound as a white solid (52 mg, 96%): 1H NMR (CD3OD, 600 MHz) δ 8.23 (s, 1H), 8.03 (s, 1H), 7.83 (m, 1H), 7.53 (m, 1H), 7.35 (m, 1H), 7.18-7.09 (m, 5H), 3.30 (t, 1H, J=6.0 Hz), 2.53 (t, 2H, J=7.5 Hz), 1.92-1.86 (m, 2H), 1.65-1.55 (m, 2H), 1.34-1.29 (m, 6H), 0.87 (s, 9H), 0.09 (s; 3H), −0.03 (s, 3H); 13C NMR (CD3OD, 150 MHz) δ 166.2, 151.6, 143.3, 136.6, 135.4, 131.3, 130.8, 128.8, 128.7, 126.9, 126.1, 124.0, 122.9, 122.6, 69.2, 36.8, 36.3, 32.0, 29.6, 29.5, 25.7, 25.6, 18.5, −5.3, −5.4.

Sources & evidence

ORD record: ord-66dc32c544ca4ed4aca14975fefee916
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915270B2

Reaction notes

Loading…