Water → 4-(2-Fluoropyridin-3-YL)tetrahydro-2H-pyran-4-carbaldehyde

HRID 410226노트

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HRID 410226 반응식
[O:1]1[CH2:6][CH2:5][CH:4]([CH:7]=[O:8])[CH2:3][CH2:2]1.Br[C:10]1[C:11]([F:16])=[N:12][CH:13]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:16][C:11]1[C:10]([C:4]2([CH:7]=[O:8])[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:15][CH:14]=[CH:13][N:12]=1

참가 물질

8

반응물 5

HCID 962WaterHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-2회HCID 27627783-Bromo-2-fluoropyridineHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehyde

생성물 1

HCID 593270314-(2-Fluoropyridin-3-YL)tetrahydro-2H-pyran-4-carbaldehyde

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매2회HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

Into a sealed tube was added tetrahydro-2H-pyran-4-carbaldehyde (0.25 g, 2.190 mmol), 3-bromo-2-fluoropyridine (0.321 g, 1.825 mmol), palladium(ii) acetate (0.016 g, 0.073 mmol), cesium carbonate (0.714 g, 2.190 mmol), water (1.644 μL, 0.091 mmol), BINAP (0.068 g, 0.110 mmol) in Dioxane (7.30 mL). The resulting mixture was heated to 100° C. overnight. More catalyst and ligand (palladium(ii) acetate (0.016 g, 0.073 mmol), binap (0.068 g, 0.110 mmol)) were added and the resulting mixture was heated to 113° C. until the starting material was completely consumed. Aqueous work up followed by DCM extraction. Purification by Biotage (0-100% MeOH/DCM) & prep-plate TLC (5% MeOH/DCM) produced product which was advanced to the next step.

후처리

  1. temperaturethe resulting mixture was heated to 113° C. until the starting material
  2. customwas completely consumed
  3. extractionAqueous work up followed by DCM extraction
  4. customPurification by Biotage (0-100% MeOH/DCM)
  5. customproduced product which

출처 및 근거

ORD 기록
ord-53f38231f3934b48adf1fea40065f156
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759532B2

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