Ethyl Acetate → HCID 57808267, 화합물

HRID 730317

반응식

HRID 730317 반응식
[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

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 21865093HCID 21865093, 화합물HCID 288758632-Chloro-4-(4-trifluoromethylphenyl)pyridine

생성물 1

HCID 57808267HCID 57808267, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
180 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f53bcbb165f84166a16279384091df26
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582657B2

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