Potassium Carbonate → HCID 58269955, compound

HRID 472030Notes

Reaction equation

HRID 472030 reaction equation
[CH2:1]([NH:4][C:5]1[C:6]([Cl:14])=[N:7][C:8]([Br:13])=[C:9]([CH3:12])[C:10]=1Br)[CH:2]=[CH2:3].C([O-])([O-])=O.[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:13][C:8]1[C:9]([CH3:12])=[C:10]2[C:2]([CH3:3])=[CH:1][NH:4][C:5]2=[C:6]([Cl:14])[N:7]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 58269933HCID 58269933, compound

Product 1

HCID 58269955HCID 58269955, compoundYield 83.9%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of allyl-(4,6-dibromo-2-chloro-5-methyl-pyridin-3-yl)-amine (5.0 g, 14.7 mmol), Pd(OAc)2 (0.33 g, 1.47 mmol), tetrabutylammonium bromide (5.2 g, 16.2 mmol), K2CO3 (6.1 g, 44 mmol) in DMF (50 mL) is degassed, then stirred at 80° C. overnight. The mixture is diluted with EtOAc and washed with water and brine, dried over MgSO4 and concentrated. Chromatography of the residue on silica gel (Hexane/EtOAc, 4:1) gives 3.2 g of 5-bromo-7-chloro-3,4-dimethyl-1H-pyrrolo[2,3-c]pyridine. 1H NMR: (CDCl3) 8.32 (1H, br), 7.14 (1H, q, J=1.1 Hz), 2.70 (3H, s), 2.46 (3H, d, J=1.1 Hz).

Workup

  1. customis degassed
  2. additionThe mixture is diluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0c904d94814d4d109de8e06731075c0b
Source dataset
uspto-grants-2014_01
Patent number
US08633193B2

Reaction notes

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