Tetrabutylammonium Fluoride → Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

Temperature

0 °C

To a solution of ethyl 4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (4.30 g, 11.3 mmol) in THF (57 mL) at about 0° C. was added TBAF (1.0 M in THF, 12.6 mL, 12.6 mmol) dropwise and the reaction mixture was stirred at about 0° C. for about 1 h. The reaction was warmed to room temperature and stirred for about 30 min. The solvent was removed under reduced pressure and the resulting oil was partitioned between EtOAc and brine (100 mL each). The organic layer was dried over anhydrous Na2SO4, filtered and concd under reduced pressure. The residue was triturated with DCM and filtered to give ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (1.32 g, 52%) as an off white solid: LC/MS (Table 1, Method b) Rt=2.07 min; MS m/z: 225 (M+H)+.

1. temperatureThe reaction was warmed to room temperature
2. stirringstirred for about 30 min
3. customThe solvent was removed under reduced pressure
4. customthe resulting oil was partitioned between EtOAc and brine (100 mL each)
5. dry with materialThe organic layer was dried over anhydrous Na2SO4
6. filtrationfiltered
7. customThe residue was triturated with DCM
8. filtrationfiltered

ORD record

ord-99e8d60144f948eeb03b344b8079aa67

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426411B2