Water → 1H-Pyrrolo[2,3-c]pyridine-4-carbonitrile

HRID 2409006Notes

Reaction equation

HRID 2409006 reaction equation
Br[C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.O.[CH3:12][N:13](C=O)C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[C-]#N.[Zn+2].[C-]#N.[Zn]>[NH:8]1[C:4]2[CH:5]=[N:6][CH:7]=[C:2]([C:12]#[N:13])[C:3]=2[CH:10]=[CH:9]1

Participants

7

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 125100554-Bromo-1H-pyrrolo(2,3-c)pyridine

Product 1

HCID 468357241H-Pyrrolo[2,3-c]pyridine-4-carbonitrileYield 99.8%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
120 °C

Procedure

A mixture of 4-bromo-1H-pyrrolo[2,3-c]pyridine (320 mg, 1.62 mmol), Pd(dppf)Cl2 (131 mg, 0.179 mmol), zinc cyanide (190 mg, 1.62 mmol), and zinc powder (21 mg, 0.324 mmol) in DMF (20 mL) was stirred at 120° C. for 2 h. The reaction mixtue was cooled to RT and H2O (100 mL) was added. The reaction mixture extracted with EtOAc (3×50 mL). The organic layers were concentrated tinder reduced pressure and the crude residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (1:1) to afford 232 mg (99.8%) of 1H-pyrrolo[2,3-c]pyridine-4-carbonitrile as yellow solid: MS (ESI) m/z: 144.2 [M+1]+.

Workup

  1. temperatureThe reaction mixtue was cooled to RT
  2. extractionThe reaction mixture extracted with EtOAc (3×50 mL)
  3. concentrationThe organic layers were concentrated tinder reduced pressure
  4. customthe crude residue was purified by SiO2 chromatography
  5. washeluting with petroleum ether/EtOAc (1:1)

Sources & evidence

ORD record
ord-90888dc18bd7438aabe9f3f11607cc89
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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