Thionyl Chloride → 6-(Chloromethyl)imidazo[1,2-b]pyridazine

HRID 1842410ノート

反応式

HRID 1842410 の反応式
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([CH2:10]O)=[N:5]2.S(Cl)([Cl:14])=O>>[Cl:14][CH2:10][C:6]1[CH:7]=[CH:8][C:9]2[N:4]([CH:3]=[CH:2][N:1]=2)[N:5]=1

参加物

3

反応物 2

HCID 24386Thionyl ChlorideHCID 59580099Imidazo[1,2-b]pyridazin-6-ylmethanol

生成物 1

HCID 595801656-(Chloromethyl)imidazo[1,2-b]pyridazine収率 69%

実験手順

Thionyl chloride (10 ml) was added to imidazo[1,2-b]pyridazin-6-ylmethanol (1.5 g, 9.0 mmol) at 20° C. under an atmosphere of nitrogen at RT. The reaction mixture was stirred at reflux for 3 h (the reaction was monitored by TLC) upon which the volatiles were removed under reduced pressure. The reaction mixture was diluted with water and extracted with EtOAc. The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography using 15% ethyl acetate in n-hexane and silica gel (230-400 mesh) to afford 6-(chloromethyl)imidazo[1,2-b]pyridazine (1.2 g, 69%,) as an off-white solid. 1H NMR, 200 MHz, DMSO-d6: δ 8.35 (s, 1H), 8.3 (d, 1H), 7.85 (s, 1H), 7.35 (d, 1H), 4.95 (s, 2H). MS: [M+H]+: m/z=149.9.

後処理

  1. temperatureat reflux for 3 h (the reaction
  2. customwere removed under reduced pressure
  3. additionThe reaction mixture was diluted with water
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-b33a54252ad14c5d9d9abb936b40449a
出典データセット
uspto-grants-2015_02
特許番号
US08946222B2

反応ノート

読み込み中…