2-Chloro-4-nitropyridine → HCID 16110653, compound

HRID 605657Notes

Reaction equation

HRID 605657 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][N: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.ClC1C=C([N+]([O-])=O)C=CN=1>>[N+:33]([C:31]1[CH:30]=[CH:29][N: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]=1)([O-:35])=[O:34]

Participants

4

Reactant 3

HCID 7351522-Chloro-4-nitropyridineHCID 16110685HCID 16110685, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110653HCID 16110653, compoundYield 66%

Procedure

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(4-nitropyridin-2-yl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (190 mg, 0.287 mmol) and 2-chloro-4-nitropyridine following General Procedure A. Flash chromatography (10% EtOAc/hexanes) yielded the title compound as a thick oil (98 mg, 66%): 1H NMR (CDCl3, 400 MHz) δ 8.91 (dd, 1H, J=5.3, 0.6 Hz), 8.33 (d, 1H, J=2.1), 7.93 (dd, 1H, J=5.3, 2.1 Hz), 7.78 (s, 1H), 7.28-7.24 (m, 2H), 7.18-7.15 (m, 3H), 4.90 (dd, 1H, J=7.3, 5.8 Hz), 2.60 (t, 2H, J=7.8 Hz), 1.96 (m, 2H), 1.62 (m, 2H), 1.36 (m, 4H), 0.92 (s, 9H), 0.12 (s, 3H), 0.03 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 166.9, 154.6, 152.2, 150.1, 149.1, 142.7, 128.3, 128.2, 127.5, 125.5, 114.8, 111.4, 68.7, 36.4, 35.9, 31.3, 29.1, 25.7, 25.7, 25.0, 18.2, −5.0, −5.1.

Sources & evidence

ORD record
ord-f969f271b8e243b78f8a0f3f129e4c07
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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