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

HRID 1798696노트

반응식

HRID 1798696 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c48cf72a4dcd491b9241998dadf82698
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343973B2

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