2-Bromo-4-methylpyridine → HCID 16110708, compound

HRID 605652Notes

Reaction equation

HRID 605652 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:32]=[C:31]([CH3:33])[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(C)C=CN=1>>[CH3:33][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

Participants

4

Reactant 3

HCID 27340872-Bromo-4-methylpyridineHCID 16110682HCID 16110682, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110708HCID 16110708, compoundYield 59%

Procedure

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(4-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-4-methylpyridine following General Procedure A. Flash chromatography (10% EtOAc/hexanes) yielded the title compound as a thick oil (41 mg, 59%): 1H NMR (CDCl3, 400 MHz) δ 8.48 (d, 1H, J=5 Hz), 7.63 (s, 1H), 7.50 (d, 1H, J=0.6 Hz), 7.29-7.25 (m, 2H), 7.18-7.15 (m, 3H), 7.05 (ddd, 1H, J=5.0, 1.5, 0.6 Hz), 4.86 (dd, 1H, J=7.3, 5.8 Hz), 2.59 (t, 2H, J=7.8 Hz), 2.41 (s, 3H), 1.93 (m, 2H), 1.61 (m, 2H), 1.36 (m, 4H), 0.91 (s, 9H), 0.11 (s, 3H), 0.01 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 165.5, 150.7, 149.6, 148.1, 147.2, 142.7, 128.2, 125.5, 125.0, 123.8, 119.9, 68.7, 36.4, 35.9, 31.4, 29.1, 25.7, 25.7, 25.1, 21.1, 18.2, −5.0, −5.2.

Sources & evidence

ORD record
ord-497937511bd5431d9125bfa66a41c8a8
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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