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

HRID 1842410노트

반응식

HRID 1842410 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-b33a54252ad14c5d9d9abb936b40449a
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946222B2

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