1-Fluoro-2-iodobenzene → 1-(5-(2-Fluorophenyl)oxazol-2-yl)-7-phenylheptan-1-one

HRID 605614노트

반응식

HRID 605614 반응식
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])=[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.FC1C=CC=CC=1I>>[F:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:24]1[O:23][C:22]([C:9](=[O:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:26][CH:25]=1

참가 물질

4

반응물 3

HCID 676731-Fluoro-2-iodobenzeneHCID 161106012-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(2-fluorophenyl)oxazoleHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

생성물 1

HCID 161106331-(5-(2-Fluorophenyl)oxazol-2-yl)-7-phenylheptan-1-one수율 98%

실험 절차

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(2-fluorophenyl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (75 mg, 0.113 mmol) and 1-fluoro-2-iodobenzene following General Procedure A. Flash chromatography (2% EtOAc/hexanes) yielded the title compound as a clear oil (52 mg, 98%): 1H NMR (CDCl3, 400 MHz) 7.77 (dt, 1H, J=9.6, 5.6 Hz), 7.42 (d, 1H, J=4.0 Hz), 7.31-7.21 (m, 4H), 7.18-7.13 (m, 4H), 4.85 (t, 1H, J=6.0 Hz), 2.59 (t, 2H, J=7.2 Hz), 1.90-1.93 (m, 2H), 1.62-1.60 (m, 2H), 1.33-1.36 (m, 6H), 0.90 (s, 9H), 0.11 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 169.7, 163.4 (d, J=250 Hz), 150.6, 157.9, 134.4 (d, J=8.3 Hz), 133.5, 133.3, 131.2 (d, J=12.6 Hz), 131.1, 131.1, 130.7, 129.6 (d, J=3.2 Hz), 121.7 (d, J=13.0 Hz), 120.1 (d, J=20.9 Hz), 73.8, 41.6, 41.0, 36.5, 34.3, 34.3, 30.9, 30.3, 23.3, 0.2, 0.0.

출처 및 근거

ORD 기록
ord-74843a14873a451885a3a1e097e06fd1
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915270B2

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