4-Bromobenzamide → HCID 16110706, compound

HRID 605613Notes

Reaction equation

HRID 605613 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:35]=[CH:34][C:30]([C:31]([NH2:33])=[O:32])=[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(C(N)=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:28]=[CH:29][C:30]([C:31]([NH2:33])=[O:32])=[CH:34][CH:35]=3)=[CH:25][N:26]=2)=[O:8])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 696834-BromobenzamideHCID 16110615HCID 16110615, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110706HCID 16110706, compoundYield 83%

Procedure

4-(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 (47 mg, 0.071 mmol) and 4-bromobenzamide following General Procedure A. Flash chromatography (30-50% EtOAc/hexanes) yielded the title compound as a white solid (29 mg, 83%): 1H NMR (CDCl3, 600 MHz) δ 7.67 (d, 2H, J=7.8 Hz), 7.57 (d, 2H, J=7.8 Hz), 7.38 (s, 1H), 7.25-7.24 (m, 2H), 7.15-7.14 (m, 3H), 6.16 (br s, 2H), 4.84 (t, 1H, J=6.0 Hz), 2.58 (t, 2H, J=7.5 Hz), 1.93-1.87 (m, 2H), 1.58-1.56 (m, 2H), 1.46-1.34 (m, 6H), 0.88 (s, 9H), 0.09 (s, 3H), −0.01 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 169.5, 143.6, 132.8, 129.9, 129.5, 129.2, 129.1, 129.0, 128.3, 127.7, 126.4, 125.0, 69.4, 37.3, 36.8, 32.2, 30.0, 26.6, 26.0, 19.1, −4.1, −4.2.

Sources & evidence

ORD record
ord-ac06e7da071242689e6e76828f9da41b
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

Loading…