Hydrochloric Acid → 7-Fluoro-2-(3-methoxy-4-pyridin-2-ylphenyl)-1,3-benzoxazole hydrochloride

HRID 7768

反応式

C[Si](OP(=O)=O)(C)C.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=1[OH:17].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)[C:23](O)=O.[ClH:35]>CCOCC>[ClH:35].[F:16][C:12]1[C:11]2[O:17][C:23]([C:22]3[CH:26]=[CH:27][C:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)=[C:20]([O:19][CH3:18])[CH:21]=3)=[N:9][C:10]=2[CH:15]=[CH:14][CH:13]=1

参加物

反応条件

温度: 200 °C

実験手順

To 7 mL trimethylsilyl polyphosphate was added 2-amino-6-fluorophenol (166 mg, 1.31 mmol) and 3-methoxy-4-pyridin-2-ylbenzoic acid (300 mg, 1.31 mmol). The mixture was heated at 200° C. for 2 h, quenched over ice, and made basic (pH 14) with 1N NaOH. The aqueous phase was extracted with EtOAc (3×150 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The resultant oil was taken up in ether and reconcentrated to give a tan solid. The free base was dissolved in ether and HCl (1N in ether) was added. The solution was filtered to give 7-fluoro-2-(3-methoxy-4-pyridin-2-ylphenyl)-1,3-benzoxazole hydrochloride as a yellow solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.71 (d, 1H), 8.00 (t, 1H), 7.97–7.84 (m, 4H), 7.70 (d, 1H), 7.49–7.37 (m, 3H), 4.00 (s, 3H); MS (ESI) 321 (M+H)+.

後処理

customquenched over ice
extractionThe aqueous phase was extracted with EtOAc (3×150 mL)
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a tan solid
filtrationThe solution was filtered

出典と根拠

ORDレコード: ord-9836977a6c9943028d1255113ebbcc1a
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 4

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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