2-Bromobenzonitrile → 2-(2-(7-Phenylheptanoyl)oxazol-5-yl)benzonitrile

HRID 605620Notes

Reaction equation

HRID 605620 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=2[C:29]#[N: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>>[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:34]=[CH:33][CH:32]=[CH:31][C:28]=3[C:29]#[N:30])=[CH:25][N:26]=2)=[O:8])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 162722-BromobenzonitrileHCID 161106712-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)benzonitrileHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 161106362-(2-(7-Phenylheptanoyl)oxazol-5-yl)benzonitrileYield 81%

Procedure

2-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)benzonitrile. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (60 mg, 0.091 mmol) and 2-bromobenzonitrile following General Procedure A. Flash chromatography (2-5% EtOAc/hexanes) yielded the title compound as a clear oil (35 mg, 81%): 1H NMR (CDCl3, 600 MHz) δ 7.90 (s, 1H), 7.85 (d, 1H, J=7.8 Hz), 7.74 (d, 1H, J=7.8 Hz), 7.66 (t, 1H, J=7.8 Hz), 7.40 (t, 1H, J=7.8 Hz), 7.27-7.25 (m, 2H), 7.16-7.15 (m, 3H), 4.87 (t, 1H, J=6.0 Hz), 2.59 (t, 2H, J=7.8 Hz), 1.96-1.90 (m, 2H), 1.62-1.60 (m, 2H), 1.38-1.36 (m, 6H), 0.90 (s, 9H), 0.10 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 166.7, 148.06, 143.6, 135.0, 134.1, 131.7, 129.2, 129.1, 129.0, 127.3, 126.9, 126.4, 124.2, 119.2, 108.3, 69.5, 37.3, 36.8, 32.3, 30.0, 26.6, 26.6, 26.0, 19.1, −4.1, −4.2.

Sources & evidence

ORD record
ord-d3342d52202f422da8bd39cbea7631b5
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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