Water → HCID 57985907, compound

To a RT solution of MeNH2.HCl (2.17 g, 31.9 mmol) in MeOH (40 mL) was added NaOH (319 mg, 7.98 mmol). The resulting mixture was stirred for 20 min. Then a solution of 3-(4-methoxy-pyrrolo[2,3-b]pyridin-1-yl)-3-phenyl-propionaldeyde (2.0 mmol) in MeOH (20 mL) was added, and the resulting mixture was stirred for 2 h. To this solution was added NaCNBH4 (125 mg, 2.0 mmol), and the mixture was stirred for 1 h, poured into water, and extracted with EtOAc. The organic layer was washed with water and brine, dried over MgSO4, filtered, concentrated, and purified via preparative TLC, affording [3-(4-Methoxy-pyrrolo[2,3-b]pyridin-1-yl)-3-phenyl-propyl]-methyl-amine (123 mg, 21% 3 steps yield). This compound was dissolved in EtOAc, and converted into the corresponding hydrochloride salt by the addition of 1 equivalent of HCl (1 M in Et2O) to give 107 mg of the corresponding HCl salt.

1. stirringthe resulting mixture was stirred for 2 h
2. additionTo this solution was added NaCNBH4 (125 mg, 2.0 mmol)
3. stirringthe mixture was stirred for 1 h
4. extractionextracted with EtOAc
5. washThe organic layer was washed with water and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. custompurified via preparative TLC

ORD record

ord-c4022377ffe34b9691e3474ee0d9d82c

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07638517B2