5-Bromo-2-fluoropyridine → 2-[4-(6-Fluoropyridin-3-yl)-3-methoxyphenyl]-1,3-benzoxazole

반응식

BrC1N=C([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:15][C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=4[N:18]=3)=[CH:10][C:9]=2[O:23][CH3:24])C=CC=1.COC1C=C(C2OC3C=CC=CC=3N=2)C=CC=1B1OC(C)(C)C(C)(C)O1.Br[C:52]1[CH:53]=[CH:54][C:55]([F:58])=[N:56][CH:57]=1>>[F:58][C:55]1[N:56]=[CH:57][C:52]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:15][C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=4[N:18]=3)=[CH:10][C:9]=2[O:23][CH3:24])=[CH:53][CH:54]=1

참가 물질

반응물 3

HCID 27831685-Bromo-2-fluoropyridine

HCID 103093892-[4-(6-Bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole

HCID 219909862-[3-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole

생성물 1

HCID 102864932-[4-(6-Fluoropyridin-3-yl)-3-methoxyphenyl]-1,3-benzoxazole

실험 절차

Utilizing the general procedure outlined in the synthesis of 2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole, 2-[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole (200 mg, 0.57 mmol) was reacted with 5-bromo-2-fluoropyridine (59 μL, 0.57 mmol) to afford the desired 2-[4-(6-fluoropyridin-3-yl)-3-methoxyphenyl]-1,3-benzoxazole as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.42 (s, 1H), 8.07–8.00 (m, 1H), 7.97–7.94 (m, 1H), 7.89 (s, 1H), 7.82–7.79 (m, 1H), 7.64–7.59(m, 1H), 7.48–7.45 (d, 1H), 7.41–7.38 (m, 1H), 7.03–6.99 (m, 1H), 3.98 (s, 3H). MS (ESI) 321 (M+H)+.