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

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%).

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

ORD record

ord-1d42f7f32eb244f9b0144d670273a255

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08198456B2