Potassium Carbonate → HCID 68556375, compound

HRID 2382104Notes

Reaction equation

HRID 2382104 reaction equation
[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:15][CH:16]=[CH2:17])[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1Cl)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:7]1[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[C:16]([CH3:17])=[CH:15]1)=[O:18])([CH3:4])([CH3:3])[CH3:2].[C:1]([O:5][C:6]([N:7]1[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[C:16](=[CH2:17])[CH2:15]1)=[O:18])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 2

HCID 11430Potassium CarbonateHCID 68557669Carbamic acid, N-(3-chloro-4-pyridinyl)-N-2-propen-1-yl-, 1,1-dimethylethyl ester

Product 2

HCID 68555346HCID 68555346, compoundHCID 68556375HCID 68556375, compoundYield 117.7%

Reagents, catalysts & solvents 4

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of allyl-(3-chloro-pyridin-4-yl)-carbamic acid tert-butyl ester (8.25 g, 30.8 mmol), tetrabutylammonium chloride (9.67 g, 30.8 mmol), palladium acetate (691 mg, 3.08 mmol) and potassium carbonate (12.8 g, 92.3 mmol) in DMF (100 mL) is heated at 800 C. for 1.5 h. The reaction is diluted with DCM and washed three times with water. The organic layer is dried (Na2SO4), filtered and concentrated. The residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane to afford a mixture 3-methyl-pyrrolo [3,2-c]pyridine-1-carboxylic acid tert-butyl ester and 3-methylene-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (4.21 g, total).

Workup

  1. temperatureis heated at 800 C
  2. washwashed three times with water
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane

Sources & evidence

ORD record
ord-3bd95e96910e4a518c80c917ada22c09
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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