Methyl 2-chloropyridine-4-carboxylate → Methyl 2-(2-(7-phenylheptanoyl)oxazol-5-yl)isonicotinate

HRID 605643

反応式

HRID 605643 の反応式
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:28]=[C:29]([CH:34]=[CH:35][N:36]=2)[C:30]([O:32][CH3:33])=[O:31])=[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(C=CN=1)C(OC)=O>>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]([C:22]2[O:23][C:24]([C:27]3[CH:28]=[C:29]([CH:34]=[CH:35][N:36]=3)[C:30]([O:32][CH3:33])=[O:31])=[CH:25][N:26]=2)=[O:8])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

4

反応物 3

HCID 2736842Methyl 2-chloropyridine-4-carboxylateHCID 16110623Methyl 2-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)isonicotinateHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

生成物 1

HCID 16110655Methyl 2-(2-(7-phenylheptanoyl)oxazol-5-yl)isonicotinate収率 71%

実験手順

Methyl 2-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)isonicotinate. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (130 mg, 0.196 mmol) and methyl 2-chloroisonicotinate following General Procedure A. Flash chromatography (10% EtOAc/hexanes) yielded the title compound as a thick oil (72 mg, 71%): 1H NMR (CDCl3, 400 MHz) δ 8.77 (d, 1H, J=5.0 Hz), 8.20 (s, 1H), 7.77 (dd, 1H, J=5.0, 1.5 Hz), 7.70 (s, 1H), 7.28-7.24 (m, 2H), 7.18-7.15 (m, 3H), 4.88 (dd, 1H, J=7.0, 5.9 Hz), 4.00 (s, 3H), 2.60 (t, 2H, J=7.8 Hz), 1.95 (m, 2H), 1.61 (m, 2H), 1.36 (m, 4H), 0.92 (s, 9H), 0.11 (s, 3H), 0.02 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 166.2, 165.2, 150.7, 150.1, 148.4, 142.7, 138.3, 128.3, 128.2, 126.0, 125.5, 121.8, 118.3, 68.7, 52.8, 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-12dfc4ae9d014bf5bb77af597151558c
出典データセット
uspto-grants-2011_03
特許番号
US07915270B2

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