Isoamyl Nitrite → 5-Iodo-1H-pyrazolo[3,4-c]pyridine

HRID 218471Notes

Reaction equation

HRID 218471 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[CH:4][N:3]=1.CC([O-])=O.[K+].[N:15](OCCC(C)C)=O.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O.CC(O)=O>[I:1][C:2]1[CH:7]=[C:6]2[CH:8]=[N:15][NH:9][C:5]2=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 8053Isoamyl NitriteHCID 516892Sodium BicarbonateHCID 517044Potassium AcetateHCID 230701206-Iodo-4-methylpyridin-3-amine

Product 1

HCID 597632735-Iodo-1H-pyrazolo[3,4-c]pyridineYield 83.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2-iodo-4-methyl-5-pyridinamine (5 g, 21.4 mmol) in toluene (340 mL) was added HOAc (19 mL), and the mixture was stirred vigorously until it became clear. Then KOAc (15.78 g, 160.23 mmol) was added. To this white suspension, isoamyl nitrite (3.16 mL, 23.5 mmol) was added dropwise at rt, and the resulting mixture was stirred for 2 days. The reaction mixture was diluted with EtOAc and treated with NaHCO3 (sat.) to pH 10. The reaction mixture was extracted with EtOAc, washed with brine, dried, and concentrated in vacuo to afford the crude product. Purification by flash chromatography afforded 5-iodo-1H-pyrazolo[3,4-c]pyridine (4.37 g, 83.5%).

Workup

  1. stirringthe resulting mixture was stirred for 2 days
  2. extractionThe reaction mixture was extracted with EtOAc
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto afford the crude product
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-1d42f7f32eb244f9b0144d670273a255
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Reaction notes

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