Ethyl Acetate → HCID 57808267、化合物

HRID 730317

反応式

HRID 730317 の反応式
[N:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[C:7]([OH:14])[CH:8]=[CH:9][CH:10]=2)[N:5]=1)=[N+]=[N-].Cl[C:16]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[CH:19]=[CH:18][N:17]=1.[H-].[Na+].CCOC(C)=O>CN(C=O)C.[Cl-].[Na+].O>[F:31][C:28]([F:29])([F:30])[C:25]1[CH:24]=[CH:23][C:22]([C:20]2[CH:21]=[CH:16][N:17]=[C:18]([O:14][C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:6]=3[N:5]=[C:4]([NH2:1])[CH:13]=[CH:12]4)[CH:19]=2)=[CH:27][CH:26]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 21865093HCID 21865093、化合物HCID 288758632-Chloro-4-(4-trifluoromethylphenyl)pyridine

生成物 1

HCID 57808267HCID 57808267、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
180 °C

実験手順

A mixture of 2-azido-quinolin-8-ol (0.28 g, 1.5 mmol), 2-chloro-4-(4-trifluoromethyl-phenyl)-pyridine (Example 410 (c), 0.26 g, 1 mmol), and sodium hydride (64 mg, 1.6 mmol) in DMF (2 mL) was heated in a 180° C. oil bath for 48 h. The reaction mixture was then transferred to a 5-mL tube, and irradiated in the Microwave Smith Synthesizer at 250° C. for 10 min. EtOAc and brine were added, and the aqueous layer was extracted with EtOAc. Combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The compound was purified on a Biotage 40S column (98:2 dichloromethane:MeOH) followed by recrystallization from EtOAc/hexanes to give the title compound as a light-yellow shiny crystal. MS (ESI, pos. ion) m/z: 382 (M+1). Mp: 196.5-199.5° C. Anal. Calcd for C21H14F3N3O: C, 66.14; H, 3.70; N, 11.02. Found: C, 66.18; H, 3.69; N, 11.08.

後処理

  1. customThe reaction mixture was then transferred to a 5-mL tube
  2. customirradiated in the Microwave Smith Synthesizer at 250° C. for 10 min
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialCombined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe compound was purified on a Biotage 40S column (98:2 dichloromethane:MeOH)
  8. customfollowed by recrystallization from EtOAc/hexanes

出典と根拠

ORDレコード
ord-f53bcbb165f84166a16279384091df26
出典データセット
uspto-grants-2009_09
特許番号
US07582657B2

関連ノート

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