3-Bromopyridine → 2-Methoxy-8-methyl-6-(3-pyridyl)quinoline

HRID 986000ノート

反応式

HRID 986000 の反応式
C([Li])(C)(C)C.Br[C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([CH3:17])[CH:16]=1)[N:13]=[C:12]([O:18][CH3:19])[CH:11]=[CH:10]2.Br[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1>CCCCC.C1COCC1.[Cl-].[Zn+2].[Cl-].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.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.[Pd]>[CH3:19][O:18][C:12]1[CH:11]=[CH:10][C:9]2[C:14](=[C:15]([CH3:17])[CH:16]=[C:7]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:8]=2)[N:13]=1

参加物

8

反応物 3

HCID 122863-BromopyridineHCID 14220967HCID 14220967、化合物HCID 178418306HCID 178418306、化合物

生成物 1

HCID 142209862-Methoxy-8-methyl-6-(3-pyridyl)quinoline

試薬・触媒・溶媒 4

HCID 3007855Zincchloride触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

t-Butyl lithium (8.0 cm3 of a 2.0M solution in pentane) was added dropwise to a stirred solution of 6-bromo-2-methoxy-8 -methylquinoline (2.0 g) in THF (20 cm3) at -70° under nitrogen. After 10 minutes the mixtures was treated with a solution of anhydrous zinc chloride (1.09 g) in THF (10 cm3) and the resulting solution was warmed to 0°. A solution containing 3-bromopyridine (1.26 g) and tetrakis(triphenylphosphine) palladium(O) (0.05 g) in THF (10 cm3) was then added and the mixture was heated under reflux for 2 hours. The reaction mixture was cooled, concentrated in vacuo, treated with chloroform (100 cm3) and a solution of ethylenediaminetetraacetic acid disodium salt (6 g) in water (100 cm3). The aqueous phase was extracted further with chloroform (3×50 cm3) and the combined and dried (MgSO4) extracts were concentrated in vacuo to give an oil. This oil was chromatographed on silica (Merck "MK 60.9385") eluting with ethyl acetate. The fractions containing the product were combined and evaporated to afford a solid which was recrystallised from hexane to afford 2-methoxy-8-methyl-6-(3-pyridyl)quinoline, m.p. 117°-118.5°, (1.12 g).

後処理

  1. temperaturethe resulting solution was warmed to 0°
  2. additionwas then added
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 2 hours
  5. temperatureThe reaction mixture was cooled
  6. concentrationconcentrated in vacuo
  7. additiontreated with chloroform (100 cm3)
  8. extractionThe aqueous phase was extracted further with chloroform (3×50 cm3)
  9. dry with materialdried (MgSO4) extracts
  10. concentrationwere concentrated in vacuo
  11. customto give an oil
  12. customThis oil was chromatographed on silica (Merck "MK 60.9385")
  13. washeluting with ethyl acetate
  14. additionThe fractions containing the product
  15. customevaporated
  16. customto afford a solid which
  17. customwas recrystallised from hexane

出典と根拠

ORDレコード
ord-b86c1f299d2047a7982d3e35bc326eb1
出典データセット
uspto-grants-1987_12
特許番号
US04710507

反応ノート

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