2-Bromopyridine → 2-[4-(6-Bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole

HRID 7781

反応式

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:18]2[O:19][C:20]3[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=3[N:22]=2)[CH:6]=[CH:7][C:8]=1B1OC(C)(C)C(C)(C)O1.[Br:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:27][C:28]1[N:29]=[C:30]([C:8]2[CH:7]=[CH:6][C:5]([C:18]3[O:19][C:20]4[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=4[N:22]=3)=[CH:4][C:3]=2[O:2][CH3:1])[CH:31]=[CH:32][CH:33]=1

参加物

反応条件

温度: 80 °C

実験手順

2-[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole (200 mg, 0.57 mmol) CsF (350 mg, 2.3 mmol), Pd(Ph3P)4 (65 mg, 0.057 mmol), and 2-bromopyridine (140 mg, 0.57 mmol) were combined in a 2-neck flask. The flask was evacuated and filled with argon and DME (5 mL) was added. The suspension was deoxygenated with a stream of argon for 10 min. The reaction mixture was stirred under argon at 80° C. for 24 h. Crude mixture was adsorbed onto silica gel and purified by automated flash chromatography using and EtOAc/hexanes gradient to afford the desired 2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.08–8.05 (d, 1H), 7.98–7.95 (m, 2H), 7.89 (s, 1H), 7.84–7.79 (m, 1H), 7.63–7.60 (m, 1H), 7.45–7.38 (m, 3H), 4.02 (s, 3H). MS (ESI) 382 (M+H)+.

後処理

customThe flask was evacuated
additionfilled with argon and DME (5 mL)
additionwas added
customThe suspension was deoxygenated with a stream of argon for 10 min
custompurified by automated flash chromatography

出典と根拠

ORDレコード: ord-ecdd950213da4b269dd5832132410a7f
出典データセット: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07087601B2

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

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