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Sodium Acetate → 5-(4-Fluorophenyl)-7-(4-imidazol-2-ylpiperidyl)thiopheno[3,2-b]pyridine

HRID 378943
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HRID 378943 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[N:5]=[C:4]2[CH:15]=[CH:16][S:17][C:3]=12.Cl.[NH:19]1[CH:23]=[CH:22][N:21]=[C:20]1[CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C([O-])(=O)C.[Na+]>C(O)CO.C(OC(=O)C)C>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:5]=[C:4]3[CH:15]=[CH:16][S:17][C:3]3=[C:2]([N:27]3[CH2:26][CH2:25][CH:24]([C:20]4[NH:21][CH:22]=[CH:23][N:19]=4)[CH2:29][CH2:28]3)[CH:7]=2)=[CH:9][CH:10]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 517045Sodium AcetateHCID 154874327-Chloro-5-(4-fluorophenyl)thieno[3,2-b]pyridineHCID 184651934-(1H-imidazol-2-yl)piperidine hydrochloride

생성물 1

HCID 99077935-(4-Fluorophenyl)-7-(4-imidazol-2-ylpiperidyl)thiopheno[3,2-b]pyridine수율 18%

시약·촉매·용매 2

HCID 174Ethylene Glycol용매
HCID 8857
Ethyl Acetate
용매

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온도
160 °C

실험 절차

A mixture of 7-chloro-5-(4-fluorophenyl)thieno[3,2-b]pyridine (146 mg, 0.53 mmol), 4-(1H-imidazol-2-yl)piperidine. hydrochloride (U.S. Pat. No. 4,431,653) (100 mg, 0.53 mmole) and sodium acetate (50 mg) in ethylene glycol (10 mL) is stirred and heated at 160° C. for about 16 hours. It is then cooled, diluted with ethylacetate (15 mL), and washed with water (3×15 mL). The organic layer is dried over sodium sulfate, filtered, and concentrated. The residue is purified by preparative thin layer chromatography to give 5-(4-fluorophenyl)-7-(4-imidazol-2-ylpiperidyl)thiopheno[3,2-b]pyridine (36 mg, 18% yield) as a white solid, m.p. 95° C. (compound 1).

후처리

  1. temperatureIt is then cooled
  2. washwashed with water (3×15 mL)
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by preparative thin layer chromatography

출처 및 근거

ORD 기록
ord-72a49192428048808f259b5fc31ce228
출처 데이터셋
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06297256B1

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