o-Iodonitrobenzene → HCID 16110693, compound

HRID 605605Notes

Reaction equation

HRID 605605 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[N+:33]([O-:35])=[O:34])=[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.IC1C=CC=CC=1[N+]([O-])=O>>[N+:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:24]1[O:23][C:22]([C:9](=[O:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:26][CH:25]=1)([O-:35])=[O:34]

Participants

4

Reactant 3

HCID 69115o-IodonitrobenzeneHCID 16110598HCID 16110598, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110693HCID 16110693, compoundYield 97%

Procedure

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(2-nitrophenyl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (75 mg, 0.113 mmol) and 1-iodo-2-nitrobenzene following General Procedure A. Flash chromatography (3-10% EtOAc/hexanes) yielded the title compound as a yellow oil (58 mg, 97%): 1H NMR (CDCl3, 300 MHz) δ 7.82 (dd, 1 H, J=9.2, 6.3 Hz), 7.70 (dd, 1H, J=9.3, 6.0 Hz), 7.67-7.64 (m, 1H), 7.51-7.49 (m, 1H), 7.32-7.25 (m, 3H), 7.19-7.16 (m, 3H), 4.82 (t, 1H, J=6.7 Hz), 2.60 (t, 2H, J=7.5 Hz), 1.88-1.86 (m, 2H), 1.64-1.60 (m, 2H), 1.35-1.26 (m, 6H), 0.90 (s, 9H), 0.10 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 75 MHz) δ 171.5, 152.5, 151.1, 148.0, 137.6, 134.6, 134.5, 133.6, 133.4, 131.3, 130.7, 129.6, 127.1, 73.8, 41.6, 41.1, 36.6, 34.3, 34.3, 30.9, 30.1, 23.4, 0.2, 0.0.

Sources & evidence

ORD record
ord-41319f850c404f6d9b4a41a29484d635
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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