Reacción #70162

Ecuación de reacción

Sodium iodide

hydrochloride salt

ethyl 4-chloro-5H-pyrrolo[3,4-b]pyridine-6(7H)-carboxylate

→

ethyl 4-iodo-5H-pyrrolo[3,4-b]pyridine-6(7H)-carboxylate

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled
2. 2
   Concentraciónconcentrated
3. 3
   Otropartitioned between CH2Cl2 and saturated aqueous sodium bicarbonate
4. 4
   OtroThe phases were separated
5. 5
   Extracciónthe aqueous phase was re-extracted twice with CH2Cl2 (total volume 750 mL)
6. 6
   Lavadofor elution
7. 7
   Otroto yield 1.98 g (71%) of Ex 11-Step 2 product as a brown solid
8. 8
   workup.ADDITIONa ˜1:1 mixture of rotamers (400 MHz, CDCl3) δ 8.08-8.11 (overlapping doublets, 1H total), 7.61 (br d, J=5.3, 1H), 4.89/4.84 (br singlets, 2H total), 4.68/4.64 (br singlets, 2H total), 4.23-4.29 (overlapping quartets, 2H total), 1.32-1.37 (overlapping triplets, 3H total)

Procedimiento

Sodium iodide (3.93 g, 26.2 mmol) and Ex 11-Step 1 product, hydrochloride salt (step 1, 2.30 g, 8.74 mmol) in acetonitrile (20 mL) were refluxed for 3 days. The reaction mixture was cooled, concentrated and partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate. The phases were separated and the aqueous phase was re-extracted twice with CH2Cl2 (total volume 750 mL). The solution was passed through a plug of silica gel (0.5″) layered with celite (0.5″) using 1:1 EtOAc/CH2Cl2 for elution to yield 1.98 g (71%) of Ex 11-Step 2 product as a brown solid: 1H NMR shows a ˜1:1 mixture of rotamers (400 MHz, CDCl3) δ 8.08-8.11 (overlapping doublets, 1H total), 7.61 (br d, J=5.3, 1H), 4.89/4.84 (br singlets, 2H total), 4.68/4.64 (br singlets, 2H total), 4.23-4.29 (overlapping quartets, 2H total), 1.32-1.37 (overlapping triplets, 3H total).

Fuente