Water → 3-ethenyl-6,7-dihydro-5H-pyrano[2,3-c]pyridazine

HRID 15150노트

반응식

HRID 15150 반응식
FC(F)(F)S(O[C:7]1[N:12]=[N:11][C:10]2[O:13][CH2:14][CH2:15][CH2:16][C:9]=2[CH:8]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].O.[CH:26](B1OB(C=C)OB(C=C)O1)=[CH2:27]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:26]([C:7]1[N:12]=[N:11][C:10]2[O:13][CH2:14][CH2:15][CH2:16][C:9]=2[CH:8]=1)=[CH2:27]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2734807TrivinylboroxinHCID 866141506,7-dihydro-5H-pyrano[2,3-c]pyridazin-3-yl trifluoromethanesulfonate

생성물 1

HCID 675268253-ethenyl-6,7-dihydro-5H-pyrano[2,3-c]pyridazine수율 77%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

Argon was bubbled for 15 minutes through a solution of 6,7-dihydro-5H-pyrano[2,3-c]pyridazin-3-yl trifluoromethanesulfonate (228 mg, 0.8 mmol) in 1,2-dimethoxyethane (6.5 ml). Tetrakis(triphenylphosphine)palladium(0) (50 mg, 0.0435 mmol) was added and the solution stirred for 20 minutes under argon. The mixture was then treated with potassium carbonate (111 mg, 0.8 mmol), water (1.9 ml) and 2,4,6-trivinylcyclotriboroxane:pyridine complex (180 mg, 0.75 mmol) (for a preparation of this reagent see F. Kerins and D. F. O'Shea, J. Org. Chem. 2002, 67, 4968-4971). After stirring for 2 hours at 80° C., the mixture was cooled and partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The layers were separated and the aqueous fraction was extracted twice with 20% methanol/dichloromethane. The combined organic solution was dried, evaporated and the residue chromatographed on silica gel, eluting with ethyl acetate to give product as a white solid (100 mg, 77%).

후처리

  1. custompyridine complex (180 mg, 0.75 mmol) (for a preparation of this reagent
  2. stirringAfter stirring for 2 hours at 80° C.
  3. temperaturethe mixture was cooled
  4. custompartitioned between dichloromethane and saturated aqueous sodium bicarbonate solution
  5. customThe layers were separated
  6. extractionthe aqueous fraction was extracted twice with 20% methanol/dichloromethane
  7. customThe combined organic solution was dried
  8. customevaporated
  9. customthe residue chromatographed on silica gel
  10. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-14ae7afc5a144a529e619ec1e51e5c60
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732460B2

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