2-Bromobenzamide → 2-(2-(7-Phenylheptanoyl)oxazol-5-yl)benzamide

HRID 605611Notes

Reaction equation

HRID 605611 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=2[C:29]([NH2:31])=[O:30])=[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=CC=1C(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:35]=[CH:34][CH:33]=[CH:32][C:28]=3[C:29]([NH2:31])=[O:30])=[CH:25][N:26]=2)=[O:8])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 776162-BromobenzamideHCID 161106032-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)benzamideHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 161106352-(2-(7-Phenylheptanoyl)oxazol-5-yl)benzamideYield 100%

Procedure

2-(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 (52 mg, 0.083 mmol) and 2-bromobenzamide following General Procedure A. Flash chromatography (20-40% EtOAc/hexanes) yielded the title compound as a white solid (39 mg, 100%): 1H NMR (CDCl3, 600 MHz) δ 7.70 (d, 1H, J=7.8 Hz), 7.60 (s, 1H), 7.51-7.48 (m, 2H), 7.39-7.36 (m, 1H), 7.25-7.23 (m, 2H), 7.16-7.13 (m, 3H), 6.48 (br s, 1H), 6.19 (br s, 1H), 4.88 (t, 1H, J=6.0 Hz), 2.57 (t, 2H, J=7.5 Hz), 1.93-1.87 (m, 2H), 1.59-1.56 (m, 2H), 1.44-1.30 (m, 6H), 0.87 (s, 9H), 0.09 (s, 3H), −0.02 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 170.4, 143.6, 137.6, 134.4, 132.5, 131.3, 130.7, 129.7, 129.2, 129.1, 128.6, 128.5, 126.4, 120.1, 69.3, 37.3, 36.8, 32.2, 30.0, 26.6, 26.6, 25.9, 19.0, −4.0, −4.3.

Sources & evidence

ORD record
ord-b790e602582747f5bce7744255d95e2f
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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