Dimethylacetamide → 1H-pyrrolo(2,3-b)pyridine-4-carbonitrile

Temperature

150 °C

4-Chloro-1H-pyrrolo[2,3-b]pyridine (10.13 g, 66.4 mmol) was dissolved into DMAC (100 mL). This solution was filtered to remove insoluble particles. N2 was purged into the solution while adding the following reagents: 4.68 g Zn(CN)2, 1.476 g dppf, 0.519 g Zn, and 1.227 g Pd2(dba)3. The greenish brown mixture was heated to 150° C. for 4 h. After cooled to RT, the mixture was filtered through a pad of Celite® and silica to remove Zn and Pd. The pad was washed with EtOAc and CH2Cl2. The filtrate was concentrated and the residue was taken into 500 mL EtOAc. This organic solution was washed with 10% NH4OH (500 mL) and sat'd NaCl (500 mL), dried over Na2SO4, filtered and concentrated to afford a dark residue, which was taken into 100-200 mL of EtOAc and resulting precipitate of 1H-pyrrolo[2,3-b]pyridine-4-carbonitrile was collected.

1. filtrationThis solution was filtered
2. customto remove insoluble particles
3. customN2 was purged into the solution
4. additionwhile adding the following reagents
5. temperatureAfter cooled to RT
6. filtrationthe mixture was filtered through a pad of Celite® and silica
7. customto remove Zn and Pd
8. washThe pad was washed with EtOAc and CH2Cl2
9. concentrationThe filtrate was concentrated
10. washThis organic solution was washed with 10% NH4OH (500 mL) and sat'd NaCl (500 mL)
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated
14. customto afford a dark residue, which

ORD record

ord-806f3f9328e2426595415e0d9156886a

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247556B2