2-Chloro-4-methoxypyridine → 1-(5-(4-Methoxypyridin-2-yl)oxazol-2-yl)-7-phenylheptan-1-one

HRID 605654

反応式

HRID 605654 の反応式
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:32]=[C:31]([O:33][CH3:34])[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(OC)C=CN=1>>[CH3:34][O: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

参加物

4

反応物 3

HCID 19911282-Chloro-4-methoxypyridineHCID 161106192-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(4-methoxypyridin-2-yl)oxazoleHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

生成物 1

HCID 161106511-(5-(4-Methoxypyridin-2-yl)oxazol-2-yl)-7-phenylheptan-1-one収率 61%

実験手順

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(4-methoxypyridin-2-yl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (144 mg, 0.302 mmol) and 2-chloro-4-methoxypyridine following General Procedure A. Flash chromatography (10% EtOAc/hexanes) yielded the title compound as a thick oil (88 mg, 61%): 1H NMR (CDCl3, 400 MHz) δ 8.43 (d, 1H, J=5.6 Hz), 7.63 (s, 1H), 7.28-7.24 (m, 2H), 7.18-7.15 (m, 3H), 6.75 (dd, 1H, J=5.8, 2.6 Hz), 4.85 (dd, 1H, J=7.3, 5.8 Hz), 3.9 (s, 3H), 2.59 (t, 2H, J=7.6 Hz), 1.93 (m, 2H), 1.61 (m, 2H), 1.36 (m, 4H), 0.90 (s, 9H), 0.10 (s, 3H), 0.01 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 166.3, 165.5, 151.1, 150.6, 148.9, 142.7, 128.3, 128.2, 125.5, 125.3, 109.0, 105.1, 68.7, 55.3, 36.4, 35.9, 31.4, 29.1, 25.7, 25.7, 25.1, 18.2, −5.0, −5.1.

出典と根拠

ORDレコード
ord-34fa70d696644f49bb1fe7aa5b6bdec7
出典データセット
uspto-grants-2011_03
特許番号
US07915270B2

関連ノート

読み込み中…