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

HRID 1798696ノート

反応式

HRID 1798696 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-c48cf72a4dcd491b9241998dadf82698
出典データセット
uspto-grants-2013_01
特許番号
US08343973B2

反応ノート

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