Potassium Carbonate → HCID 68559071, compound

HRID 2382094Notes

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]

Participants

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

customThe reaction is quenched with DCM
washwashed with water
dry with materialThe organic layer is dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
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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