Water → HCID 22240138, 화합물

HRID 891948노트

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HRID 891948 반응식
Cl[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Cl:15])[CH:9]=2)[N:5]=[N:6][CH:7]=1.C([Sn](CCCC)(CCCC)[CH2:21][O:22][CH2:23][O:24][CH3:25])CCC.C(OCC)(=O)C.O>CN(C=O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:15][C:10]1[CH:9]=[C:8]([C:4]2[N:5]=[N:6][CH:7]=[C:2]([CH2:21][O:22][CH2:23][O:24][CH3:25])[CH:3]=2)[CH:13]=[CH:12][C:11]=1[F:14]

참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4193592Tributyl[(methoxymethoxy)methyl]stannaneHCID 22240223HCID 22240223, 화합물

생성물 1

HCID 22240138HCID 22240138, 화합물수율 60%

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

5-Chloro-3-(3-chloro-4-fluoro-phenyl)-pyridazine (535 mg, 2.2 mmol) and bis-(triphenylphosphine) -palladium(II)-dichloride (145 mg, 0.22 mmol) were treated with a solution of tributyl-methoxymethoxymethyl-stannane (Sawyer J. S.; Kucerovy A.; Macdonald T. L.; McGarvey G. J. J. Am. Chem. Soc. (1988), 110, 842-853) (964 mg, 2.64 mmol) in DMF (5.3 ml). The mixture was heated at 100° C. for 4 hours then cooled to room temperature and a saturated KEF solution (5.3 ml) was added. The mixture was stirred for 30 minutes at room temperature and ethyl acetate and water were added. The mixture was filtered and extracted 3 times with ethyl acetate. The combined extracts were dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was chromatographed over silica gel (hexane-ethylacetate 7:3) to provide 3-(3-chloro-4-fluoro-phenyl)-5-methoxymethoxymethyl-pyridazine (370 mg, 60%) as a pale yellow solid, MS: m/e=283.0 (M+H+).

후처리

  1. temperaturethen cooled to room temperature
  2. filtrationThe mixture was filtered
  3. extractionextracted 3 times with ethyl acetate
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe residue was chromatographed over silica gel (hexane-ethylacetate 7:3)

출처 및 근거

ORD 기록
ord-7c1241f517294c66b6d7f927a25c434f
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005432B2

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