Isopropylamine → HCID 67290874, compound

HRID 511850Notes

Reaction equation

HRID 511850 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:4][N:3]=1.[CH:16]([NH2:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[CH:16]([NH:19][C:2]1[CH:7]=[C:6]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:4][N:3]=1)([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 10796Cesium carbonateHCID 87341778HCID 87341778, compound

Product 1

HCID 67290874HCID 67290874, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a dioxane (5 mL) solution of ethyl trans-2-(2-chloropyridin-4-yl)cyclopropanecarboxylate (250 mg, 1.1 mmol) and isopropylamine (393 mg, 6.7 mmol) were added cesium carbonate (1.1 g, 3.3 mmol), Xantophos (224 mg, 0.4 mmol) and palladium acetate (50 mg, 0.2 mmol) at room temperature respectively. The mixture was sealed and stirred at 100 ° C. for 14 hours. After being filtered off, the filtrate was concentrated under reduced pressure, the residue was applied to a silica gel chromatography column and eluted with a hexane/ethyl acetate =6/1 to furnish 100 mg (36% yield) of the title as a colorless oil.

Workup

  1. customThe mixture was sealed
  2. filtrationAfter being filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washeluted with a hexane/ethyl acetate =6/1
  5. customto furnish 100 mg (36% yield) of the title as a colorless oil

Sources & evidence

ORD record
ord-a1e3b1648a9a413ab3492802d899801b
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

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