Hydrochloric Acid → 5-Cyano-2,3-dimethyl-pyrrolo[2,3-b]pyridine

HRID 1756106Notes

Reaction equation

HRID 1756106 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[C:9]([CH3:12])[NH:8][C:5]2=[N:6][CH:7]=1.BrC1[N:19]=[C:18]2NC(C)=C(C)C2=CC=1.C([Cu])#N.Cl>O.N1C=CC=CC=1>[C:18]([C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[C:9]([CH3:12])[NH:8][C:5]2=[N:6][CH:7]=1)#[N:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 193925846-Bromo-2,3-dimethyl-pyrrolo[2,3-b]pyridineHCID 193926125-Bromo-2,3-dimethyl-1H-pyrrolo[2,3-B]pyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 193925855-Cyano-2,3-dimethyl-pyrrolo[2,3-b]pyridineYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
220 °C

Procedure

An autoclave was charged with 5-bromo-2,3-dimethyl-pyrrolo[2,3-b]pyridine (prepared in a similar manner as 6-bromo-2,3-dimethyl-pyrrolo[2,3-b]pyridine (247 mg, 1.1 mmol) and CuCN (135 mg. 1.5 mmol). The mixture was covered with pyridine and heated to 220° C. for 12 h. After cooling the raction mixture was poured into a mixture of FeCl3 hexahydrate (0.9 g), conc HCl (0.5 ml), and water (10 ml). The mixture was heated to 80° C. for 1 h and extracted with CH2Cl2. The organic layer was washed four times with 2M HCl, dried over MgSO4 and evaporated leaving 77 mg (40%) 5-cyano-2,3-dimethyl-pyrrolo[2,3-b]pyridine.

Workup

  1. temperatureAfter cooling the raction mixture
  2. temperatureThe mixture was heated to 80° C. for 1 h
  3. extractionextracted with CH2Cl2
  4. washThe organic layer was washed four times with 2M HCl
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-4ea5a05b3085410084955ddf97149409
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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