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Cesium carbonate → Ethyl 4-(2,4-diamino-3-methoxycarbonylphenyl)-furan-3-carboxylate

HRID 1778403
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HRID 1778403 반응식
[NH2:1][C:2]1[C:11](Br)=[CH:10][CH:9]=[C:8]([NH2:13])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].COC([C:18]1[O:19][CH:20]=[CH:21][C:22]=1B(O)O)=O.F[B-](F)(F)F.C([PH+]([C:40]([CH3:43])(C)C)C(C)(C)C)(C)(C)C.[C:44](=O)([O-:46])[O-:45].[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]>[NH2:1][C:2]1[C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:8]([NH2:13])[CH:9]=[CH:10][C:11]=1[C:21]1[C:22]([C:44]([O:46][CH2:40][CH3:43])=[O:45])=[CH:18][O:19][CH:20]=1
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참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 66685498[2-(Methoxycarbonyl)furan-3-yl]boronic acidHCID 66685632Methyl 2,6-diamino-3-bromobenzoate2회

생성물 1

HCID 66685491Ethyl 4-(2,4-diamino-3-methoxycarbonylphenyl)-furan-3-carboxylate수율 689.8%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 962Water용매
HCID 312751,4-Dioxane용매

실험 절차

A mixture of methyl 2,6-diamino-3-bromobenzoate (Intermediate 90, 1.0 g), 2-methoxycarbonyl-furan-3-boronic acid (0.980 g), tris-(dibenzylideneacetone)-dipalladium (0.188 g), tri-tert-butylphosphonium tetrafluoroborate (0.119 g) and cesium carbonate (4.0 g) in dioxane (45 mL) and water (6 mL) was de-gassed and flushed with argon. The resultant mixture was stirred at room temperature for 1 hour, then heated at 70° C. for 1 hour. The mixture was cooled, diluted with ethyl acetate and washed with water, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and pentane, with a gradient of 20-50% to give ethyl 4-(2,4-diamino-3-methoxycarbonylphenyl)-furan-3-carboxylate (0.861 g).

후처리

  1. customwas de-gassed
  2. customflushed with argon
  3. temperatureheated at 70° C. for 1 hour
  4. temperatureThe mixture was cooled
  5. additiondiluted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo
  10. customthe residue was purified by chromatography on silica
  11. washeluting with a mixture of ethyl acetate and pentane, with a gradient of 20-50%

출처 및 근거

ORD 기록
ord-52135b162fed41f4b890d3e57a9629fe
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09266896B2

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