Water → HCID 43339385, compound

Modification of Method A: To a mixture of 1H-pyrrolo[2,3-b]pyridine (1.0 g, 8.46 mmol) and AlCl3 (3.4 g, 25.50 mmol) in dry methylene chloride (20 mL) was added phenyl acetyl chloride (3.27 g, 21.15 mmol) at room temperature. The solution was then stirred at room temperature (RT) for 4 hrs. The mixture was poured into iced water and extracted with methylene chloride (3×20 mL). The combined organic layers were dried over MgSO4, filtered, and evaporated. The residue was then dissolved in MeOH (20 mL) and treated with 6N NaOH (5 mL) at RT for 2 hrs. Evaporated most of the solvent, the residue was acidified with 6N HCl and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and evaporated. The residue was purified by flash column to give desired product (1.3 g, 65%). MS (ES−): m/e=235.2 (M−H); LC/Method A/2.86 min.

1. extractionextracted with methylene chloride (3×20 mL)
2. dry with materialThe combined organic layers were dried over MgSO4
3. filtrationfiltered
4. customevaporated
5. dissolutionThe residue was then dissolved in MeOH (20 mL)
6. additiontreated with 6N NaOH (5 mL) at RT for 2 hrs
7. customEvaporated most of the solvent
8. extractionextracted with EtOAc
9. dry with materialThe combined organic layers were dried over MgSO4
10. filtrationfiltered
11. customevaporated
12. customThe residue was purified by flash column

ORD record

ord-68d516f472c148679f0e903a11c4ab98

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07446199B2