1-Iodo-3-nitrobenzene → HCID 16110698, compound

HRID 605606Notes

Reaction equation

HRID 605606 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([N+:33]([O-:35])=[O:34])[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.IC1C=CC=C([N+]([O-])=O)C=1>>[N+:33]([C:29]1[CH:28]=[C:27]([C:24]2[O:23][C:22]([C:9](=[O:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:26][CH:25]=2)[CH:32]=[CH:31][CH:30]=1)([O-:35])=[O:34]

Participants

4

Reactant 3

HCID 125741-Iodo-3-nitrobenzeneHCID 16110605HCID 16110605, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110698HCID 16110698, compoundYield 90%

Procedure

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(3-nitrophenyl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (191 mg, 0.288 mmol) and 1-iodo-3-nitrobenzene following General Procedure A. Flash chromatography (5-10% EtOAc/hexanes) yielded the title compound as a yellow oil (128 mg, 90%): 1H NMR (CDCl3, 500 MHz) δ 8.57-8.56 (m, 1H), 8.26-8.24 (m, 1H), 8.03-8.02 (m, 1H), 7.69 (t, 1H, J=16 Hz), 7.51 (s, 1H), 7.36-7.33 (m, 2H), 7.26-7.23 (m, 3H), 4.94 (t, 1H, J=6.0 Hz), 2.67 (t, 2H, J=7.5 Hz), 2.05-1.96 (m, 2H), 1.72-1.66 (m, 2H), 1.57-1.44 (m, 6H), 0.99 (s, 9H), 0.19 (s, 3H), 0.09 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 166.4, 149.3, 149.2, 143.2, 130.5, 130.1, 130.0, 128.8, 128.6, 126.0, 124.2, 123.2, 119.4, 69.1, 36.8, 36.3, 31.8, 29.6, 26.1, 26.1, 25.5, 18.6, −4.5, −4.6.

Sources & evidence

ORD record
ord-abe822a36b7c40a3b27a84bfbd0b0d06
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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