Cesium carbonate → N-(2-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl)cyclopropanecarboxamide

HRID 2201788Notes

Reaction equation

HRID 2201788 reaction equation
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([CH3:11])[NH:8][C:7]=12.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:60]1([C:63]([NH2:65])=[O:64])[CH2:62][CH2:61]1>C1(C)C=CC=CC=1.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]>[CH3:11][C:9]1[NH:8][C:7]2=[C:2]([NH:65][C:63]([CH:60]3[CH2:62][CH2:61]3)=[O:64])[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 80376CyclopropanecarboxamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 115428387-Chloro-2-methyl-1H-pyrrolo[2,3-C]pyridine

Product 1

HCID 71061496N-(2-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl)cyclopropanecarboxamideYield 40%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 7-chloro-2-methyl-1H-pyrrolo[2,3-c]pyridine (1.1 g, 06 mmol) in toluene were added tris (dibenzylidene acetone)dipalladium (302 mg, 0.3 mmol), Xantphos (0.286 g, 0.49 mmol), cesium carbonate (4.3 g, 13.2 mmol), and cyclopropanecarboxamide (0.842 g, 9 mmol). The resulting reaction mixture was heated to 110° C. and stirred for about 4 hours. The reaction mixture cooled to room temperature diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel (100-200) column chromatography to afford N-(2-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl)cyclopropanecarboxamide (0.45 g, 40% yield).

Workup

  1. customThe resulting reaction mixture
  2. temperatureThe reaction mixture cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel (100-200) column chromatography

Sources & evidence

ORD record
ord-99238cdc61ca42a7a12ea5363d67dcb5
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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