Water → HCID 22240138、化合物

HRID 891948ノート

反応式

HRID 891948 の反応式
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]

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4193592Tributyl[(methoxymethoxy)methyl]stannaneHCID 22240223HCID 22240223、化合物

生成物 1

HCID 22240138HCID 22240138、化合物収率 60%

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-7c1241f517294c66b6d7f927a25c434f
出典データセット
uspto-grants-2006_02
特許番号
US07005432B2

反応ノート

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