2-Bromo-3-methylpyridine → HCID 16110649, compound

HRID 605653Notes

Reaction equation

HRID 605653 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[C:32]([CH3:33])=[CH:31][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.BrC1C(C)=CC=CN=1>>[CH3:33][C:32]1[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:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:26][CH:25]=2)=[N:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 2208322-Bromo-3-methylpyridineHCID 16110617HCID 16110617, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110649HCID 16110649, compoundYield 40%

Procedure

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(3-methylpyridin-2-yl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (130 mg, 0.196 mmol) and 2-bromo-3-methylpyridine following General Procedure A. Flash chromatography (10% EtOAc/hexanes) yielded the title compound as a thick oil (28 mg, 40%): 1H NMR (CDCl3, 400 MHz) δ 8.52 (dd, 1H, J=4.7, 1.5 Hz), 7.57 (ddd, 1H, J=7.6, 1.4, 0.6 Hz), 7.55 (s, 1H), 7.29-7.24 (m, 2H), 7.18-7.15 (m, 4H), 4.89 (dd, 1H, J=7.6, 5.9 Hz), 2.59 (t, 2H, J=7.8 Hz), 2.55 (s, 3H), 1.93 (m, 2H), 1.61 (m, 2H), 1.36 (m, 4H), 0.89 (s, 9H), 0.10 (s, 3H), −0.02 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 165.6, 150.9, 147.1, 146.0, 142.8, 139.3, 130.3, 128.3, 128.2, 127.1, 125.5, 122.6, 68.6, 36.5, 35.9, 31.4, 29.1, 25.7, 25.7, 25.1, 20.4, 18.2, −5.0, −5.2.

Sources & evidence

ORD record
ord-eb93f03fb5214bd5acf2db9382c59784
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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