Potassium Carbonate → 2-[2-(6-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-3-methoxy-5-phenyl-pyrazine

HRID 1609836ノート

反応式

HRID 1609836 の反応式
Cl[CH2:2][C:3]1[C:8]([O:9][CH3:10])=[N:7][C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][N:4]=1.[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2[NH:25][CH:26]=[CH:27][N:28]=2)[N:19]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:17][C:18]1[N:19]=[C:20]([C:24]2[N:28]([CH2:2][C:3]3[C:8]([O:9][CH3:10])=[N:7][C:6]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[CH:5][N:4]=3)[CH:27]=[CH:26][N:25]=2)[CH:21]=[CH:22][CH:23]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 219192862-Fluoro-6-(1h-imidazol-2-yl)pyridineHCID 222603922-Chloromethyl-3-methoxy-5-phenyl-pyrazine

生成物 1

HCID 100899662-[2-(6-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-3-methoxy-5-phenyl-pyrazine収率 85.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
45 °C

実験手順

A mixture of 2-chloromethyl-3-methoxy-5-phenyl-pyrazine (70 mg, 0.30 mmol), 2-fluoro-6-(1H-imidazol-2-yl)-pyridine (48 mg, 0.294 mmol) and K2CO3 (123 mg, 0.9 mmol) in DMF (5 mL) is stirred at 45° C. for 16 hours. On cooling, the reaction is quenched with saturated NH4Cl (2 mL) and extracted with DCM (3×10 mL). The combined organic layers are dried and solvent removed. PTLC separation (10% MeOH in DCM) gives 91 mg of 2-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-3-methoxy-5-phenyl-pyrazine as an oil. 1H NMR (CDCl3) 8.41 (s, 1H), 8.08 (dd, 1H), 7.95–7.99 (m, 2H), 7.80 (dd, 1H), 7.42–7.49 (m, 3H), 7.22 (s, 1H), 7.15 (s, 1H), 6.77 (dd, 1H), 5.98 (s, 2H), 4.08 (s, 3H). B. 3-Methoxy-5-phenyl-2-(2-thiazol-2-yl-imidazol-1-ylmethyl)-pyrazine (Compound 2) 1. Synthesis of 2-(1H-imidazol-2-yl)-thiazole

後処理

  1. temperatureOn cooling
  2. customthe reaction is quenched with saturated NH4Cl (2 mL)
  3. extractionextracted with DCM (3×10 mL)
  4. customThe combined organic layers are dried
  5. customsolvent removed
  6. customPTLC separation (10% MeOH in DCM)

出典と根拠

ORDレコード
ord-3cbdb311c5ee49c88288efb153017b1c
出典データセット
uspto-grants-2006_01
特許番号
US06982268B2

反応ノート

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