Methyl iodide → N-methyl-1H-pyrrolo[2,3-b]pyridin-5-amine

1-Triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-ylamine (375 mg, 1.3 mmol) and triethylamine (271 μL, 1.95 mmol) in dichloromethane (10 mL) was treated with di-tert-butyl dicarbonate (340 mg, 1.5 mmol) and the mixture was stirred at RT for 2.5 h., quenched with saturated ammonium chloride (20 mL) and extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine (50 mL), dried (MgSO4.), filtered and concentrated. The residue was purified by preparative HPLC. B. 1-Triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-carbamic acid tert-butyl ester (250 mg, 0.6 mmol) was then treated with sodium hydride (24 mg, 60% oil, 0.6 mmol) and methyl iodide (48 mL, 0.77 mmol) in DMF (2.0 mL). The mixture was stirred at RT for 16 h, quenched with saturated ammonium chloride (20 mL) and extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine (50 mL), dried (MgSO4.), filtered and concentrated. The residue, which was used with no further purification, was then treated with TFA (1.0 mL) in dichloromethane (4.0 mL) and the mixture was stirred at RT for 10 h, concentrated and purified by preparative HPLC to afford methyl(1H-pyrrolo[2,3-b]pyridin-5-yl)-amine (31 mg, 33%). m/z 148 (M+H)+.

1. customquenched with saturated ammonium chloride (20 mL)
2. extractionextracted with ethyl acetate (3×25 mL)
3. washThe combined organic layers were washed with brine (50 mL)
4. dry with materialdried (MgSO4.)
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by preparative HPLC
8. stirringThe mixture was stirred at RT for 16 h
9. customquenched with saturated ammonium chloride (20 mL)
10. extractionextracted with ethyl acetate (3×25 mL)
11. washThe combined organic layers were washed with brine (50 mL)
12. dry with materialdried (MgSO4.)
13. filtrationfiltered
14. concentrationconcentrated
15. customThe residue, which was used with no further purification
16. additionwas then treated with TFA (1.0 mL) in dichloromethane (4.0 mL)
17. stirringthe mixture was stirred at RT for 10 h
18. concentrationconcentrated
19. custompurified by preparative HPLC

ORD record

ord-a23d7d75c23449ae87031bae6b72a436

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06969717B2