Cesium carbonate → Methyl 7-aminofuro[2,3-c]quinoline-6-carboxylate

HRID 927916ノート

反応式

HRID 927916 の反応式
Br[C:2]1[C:3]([NH2:13])=[C:4]([C:9]([NH2:12])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH:14]([C:16]1[O:17][CH:18]=[CH:19][C:20]=1B1OC(C)(C)C(C)(C)O1)=O.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH2:12][C:9]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]2[C:2]([C:20]3[CH:19]=[CH:18][O:17][C:16]=3[CH:14]=[N:13]2)=[CH:11][CH:10]=1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 164141993-(Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehydeHCID 66685632Methyl 2,6-diamino-3-bromobenzoate2 回

生成物 1

HCID 66685912Methyl 7-aminofuro[2,3-c]quinoline-6-carboxylate収率 85.3%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

A mixture of methyl 3-bromo-2,6-diaminobenzoate (Intermediate 25, 1.34 g), 2-formylfuran-3-boronic acid pinacol ester (1.46 g), tri-tert-butylphosphonium tetrafluoroborate (0.305 g), cesium carbonate (5.15 g) and tris-(dibenzylideneacetone)dipalladium (0.49 g) in a mixture of dioxane (80 mL) and water (30 mL) was degassed and purged with argon then heated at 60° C. for 1 hour. After cooling, the mixture was filtered through Celite and the pad was washed thoroughly with ethyl acetate. The filtrate was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100% to give methyl 7-aminofuro[2,3-c]quinoline-6-carboxylate (1.13 g) as a brown gum.

後処理

  1. customwas degassed
  2. custompurged with argon
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through Celite
  5. washthe pad was washed thoroughly with ethyl acetate
  6. washThe filtrate was washed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100%

出典と根拠

ORDレコード
ord-580dc65582a341a28548dfc9f623180e
出典データセット
uspto-grants-2016_03
特許番号
US09290472B2

反応ノート

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