2-(2,2-Dimethoxyethyl)-1,3-dithiane → HCID 22335039、化合物

HRID 586375ノート

反応式

HRID 586375 の反応式
[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

参加物

5

反応物 3

HCID 131670152-(2,2-Dimethoxyethyl)-1,3-dithianeHCID 22335102HCID 22335102、化合物HCID 178418339Butyllithium

生成物 1

HCID 22335039HCID 22335039、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-30 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-cdb036a972144dc3ba74c100652fa566
出典データセット
uspto-grants-2005_08
特許番号
US06936617B2

反応ノート

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