2-(2,2-Dimethoxyethyl)-1,3-dithiane → HCID 22335039, 화합물

HRID 586375노트

반응식

HRID 586375 반응식
[Li]CCCC.[CH3:6][O:7][CH:8]([O:16][CH3:17])[CH2:9][CH:10]1[S:15][CH2:14][CH2:13][CH2:12][S:11]1.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]2[N:23]([C:25]([CH3:30])=[C:26]([CH2:28]Cl)[N:27]=2)[CH:24]=1>C1COCC1>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]2[N:23]([C:25]([CH3:30])=[C:26]([CH2:28][C:10]3([CH2:9][CH:8]([O:7][CH3:6])[O:16][CH3:17])[S:15][CH2:14][CH2:13][CH2:12][S:11]3)[N:27]=2)[CH:24]=1

참가 물질

5

반응물 3

HCID 131670152-(2,2-Dimethoxyethyl)-1,3-dithianeHCID 22335102HCID 22335102, 화합물HCID 178418339Butyllithium

생성물 1

HCID 22335039HCID 22335039, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-30 °C

실험 절차

A solution of n-BuLi in hexanes (1.6 M, 1.4 mL) is added dropwise at −50° C. to a solution of 2-(2,2-dimethoxy-ethyl)-[1,3]dithiane (450 mg, prepared according J. Het. Chem, 1987, 1221) in THF. The mixture is then warmed to −30° C. for 1 hour. After cooling to −50° C., a solution of 6-chloro-2-chloromethyl-3-methyl-imidazo[1,2-a]pyridine (300 mg) in 3 mL of THF is added dropwise; the reaction mixture is then slowly warmed to room temperature. After quenching with aqueous NH4Cl solution, the mixture is extracted with ethyl acetate. The extract is washed with brine, dried over Na2SO4 and concentrated under vacuum. The residue is purified on flash chromatographic column, eluting with 5% MeOH in CH2Cl2, to give 6-Chloro-2-[2-(2,2-dimethoxy-ethyl)-[1,3]dithian-2-ylmethyl]-3-methyl-imidazo[1,2-a]pyridine. 1H NMR (CDCl3, ppm): 7.80 (s, 1H); 7.50(d, 1H); 7.05(d, 1H); 4.80(t, 1H); 3.40(m, 8H); 2.75-3.00(m, 4H); 2.40-2.50(m, 5H); 1.80-2.05(m, 2H). Step 2. Preparation of 6-Chloro-2-[2-(6-fluoro-pyridin-2-yl)-2H-pyrazol-3-ylmethyl]-3-methyl-imidazol[1,2-a]pyridine

후처리

  1. temperatureAfter cooling to −50° C.
  2. temperaturethe reaction mixture is then slowly warmed to room temperature
  3. customAfter quenching with aqueous NH4Cl solution
  4. extractionthe mixture is extracted with ethyl acetate
  5. washThe extract is washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customThe residue is purified on flash chromatographic column
  9. washeluting with 5% MeOH in CH2Cl2

출처 및 근거

ORD 기록
ord-cdb036a972144dc3ba74c100652fa566
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936617B2

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