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Dichloromethane → Ethyl 6-(1-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyridine-3-carboxylate

HRID 335314
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HRID 335314 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[CH:9][C:10]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=1.[CH3:16][N:17]1[C:21](B2OC(C)(C)C(C)(C)O2)=[CH:20][CH:19]=[N:18]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl>COCCOC.O.CO.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:16][N:17]1[C:21]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([N:8]=[CH:9][C:10]=3[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=2)=[CH:20][CH:19]=[N:18]1
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참가 물질

10

반응물 4

HCID 6344Dichloromethane3회HCID 10796Cesium carbonateHCID 49129081-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2회HCID 12208504Ethyl 6-bromopyrazolo[1,5-a]pyridine-3-carboxylate

생성물 1

HCID 71283198Ethyl 6-(1-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyridine-3-carboxylate

시약·촉매·용매 5

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
3회
HCID 887Methanol용매
HCID 962Water용매
HCID 80711,2-Dimethoxyethane용매
HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

A mixture comprising ethyl 6-bromopyrazolo[1,5-a]pyridine-3-carboxylate (1.5 g, 5.57 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.218 g, 5.85 mmol), cesium carbonate (7.26 g, 22.30 mmol) and PdCl2(dppf).CH2Cl2 adduct (91 mg, 0.111 mmol) in DME (10 ml) and water (4.00 ml) was heated using microwave radiation at 70° C. for 1 hr. Further PdCl2(dppf).CH2Cl2 adduct (91 mg, 0.111 mmol) was added and the mixture was heated at 80° C. for 1 hr. 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.218 g, 5.85 mmol) and PdCl2(dppf).CH2Cl2 adduct (91 mg, 0.111 mmol) were added and heating continued at 100° C. for 3 hrs. The mixture was diluted with 10% MeOH in EtOAc (200 ml) and washed with sat. NaHCO3. The organic solvent was removed under vacuum and azeotroped with toluene. The resulting solid was loaded onto silica and purified by chromatography eluting with 0-100% EtOAc in iso-hexane to afford the title compound;

후처리

  1. customat 70° C.
  2. customfor 1 hr
  3. temperatureheating
  4. washwashed with sat. NaHCO3
  5. customThe organic solvent was removed under vacuum
  6. customazeotroped with toluene
  7. custompurified by chromatography
  8. washeluting with 0-100% EtOAc in iso-hexane

출처 및 근거

ORD 기록
ord-a51e8a8797644202b84ed8ddc75e957f
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08883819B2

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