Tetramethyltin → 4-Methoxy-3-methyl-6-[3-(trifluoromethyl)phenyl]pyridazine

HRID 54656ノート

反応式

HRID 54656 の反応式
Br[C:2]1[N:3]=[N:4][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[CH:6][C:7]=1[O:8][CH3:9].[CH3:20][Sn](C)(C)C>CN(C=O)C.[CH2-]C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd+]>[CH3:9][O:8][C:7]1[CH:6]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:4]=[N:3][C:2]=1[CH3:20]

参加物

5

反応物 2

HCID 11661TetramethyltinHCID 199596693-Bromo-4-methoxy-6-[3-(trifluoromethyl)phenyl]pyridazine

生成物 1

HCID 199596804-Methoxy-3-methyl-6-[3-(trifluoromethyl)phenyl]pyridazine収率 63%

試薬・触媒・溶媒 2

HCID 11007180Palladium(2+) chloride phenylmethanide--triphenylphosphane (1/1/1/2)触媒HCID 6228Dimethylformamide溶媒

実験手順

3-Bromo-4-methoxy-6-[3-(trifluoromethyl)phenyl]pyridazine (1.0 g, 0.003 mole, Compound No. 65), tetramethyltin (1.28 g, 0.0072 mole) and trans-benzyl(chloro)bis-(triphenylphosphine)palladium(II) (20 mg) were heated to 100° C. in DMF under N2 for 18 h. The reaction was then cooled and partitioned between aqueous KF solution and ethyl acetate. The KF solution was extracted with additional ethyl acetate. The organic layers were washed with brine, dried (MgSO4), filtered through silica gel and then evaporated in vacuo. The crude oil was then chromatographed on a Prep-500 to give 4-methoxy-3-methyl-6-[3-(trifluoromethyl)phenyl]pyridazine (0.51 g, 63% yield, Compound No. 66) as a light yellow solid.

後処理

  1. temperatureThe reaction was then cooled
  2. custompartitioned between aqueous KF solution and ethyl acetate
  3. extractionThe KF solution was extracted with additional ethyl acetate
  4. washThe organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered through silica gel
  7. customevaporated in vacuo
  8. customThe crude oil was then chromatographed on a Prep-500

出典と根拠

ORDレコード
ord-f784d83324384c11a02788add6a08287
出典データセット
uspto-grants-1997_04
特許番号
US05623072

反応ノート

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