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Potassium Carbonate → HCID 68559071, compound

HRID 2382094
Notes
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Reaction equation

HRID 2382094 reaction equation
[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:15][CH:16]=[CH2:17])[C:8]1[C:9](Cl)=[N:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:7]1[C:8]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=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[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[C:16](=[CH2:17])[CH2:15]1)=[O:18])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 11430Potassium CarbonateHCID 86639381HCID 86639381, compound

Product 2

HCID 68559040HCID 68559040, compoundHCID 68559071HCID 68559071, compoundYield 45.3%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalyst
HCID 167845
palladium(II) acetate
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of allyl-(2-chloro-pyridin-3-yl)-carbamic acid tert-butyl ester (8.03 g, 30 mmol), tetrabutylammonium chloride (9.4 g, 30 mmol), palladium acetate (673 mg, 3 mmol) and potassium carbonate (12.4 g, 3 mmol) in DMF (300 mL) is heated at 80° C. for 1.5 h. The reaction is quenched with DCM and washed 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 3-methyl-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester and 3-methylene-2,3-dihydro-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester (1.58 g).

Workup

  1. customThe reaction is quenched with DCM
  2. washwashed 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-8cb00e3b22144a6ea880c96824089970
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08258130B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes