1-Iodo-4-nitrobenzene → HCID 16110643, compound

HRID 605607Notes

Reaction equation

HRID 605607 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[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.IC1C=CC([N+]([O-])=O)=CC=1>>[N+:33]([C:30]1[CH:29]=[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]=1)([O-:35])=[O:34]

Participants

4

Reactant 3

HCID 124951-Iodo-4-nitrobenzeneHCID 16110611HCID 16110611, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110643HCID 16110643, compoundYield 100%

Procedure

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(4-nitrophenyl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (90 mg, 0.136 mmol) and 1-iodo-4-nitrobenzene following General Procedure A. Flash chromatography (5-10% EtOAc/hexanes) yielded the title compound as a yellow oil (67 mg, 100%): 1H NMR (CDCl3, 500 MHz) δ 8.28 (d, 2H, J=9.0 Hz), 7.78 (d, 2H, J=9.0 Hz), 7.48 (s, 1H), 7.27-7.24 (m, 2H), 7.17-7.15 (m, 3H), 4.87 (t, 1H, J=6.0 Hz), 2.59 (t, 2H, J=7.8 Hz), 2.00-1.88 (m, 2H), 1.67-1.58 (m, 2H), 1.40-1.34 (m, 6H), 0.91 (s, 9H), 0.11 (s, 3H), 0.01 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 166.6, 149.0, 147.1, 142.6, 133.7, 128.3, 128.2, 125.5, 125.1, 124.4, 124.3, 68.6, 36.3, 35.8, 31.3, 29.1, 25.6, 25.6, 25.0, 18.1, −5.0, −5.1.

Sources & evidence

ORD record
ord-0ed62a153a9f4f6f8cdde3b9069cb427
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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