tert-butyl 7-chloro-3-iodo-1H-pyrrolo[2,3-c]pyridine-1-carboxylate → tert-butyl 3-(2-tert-butoxy-2-oxoethyl)-7-chloro-1H-pyrrolo[2,3-c]pyridine-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl 7-chloro-3-iodo-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (500 mg, 1.3 mmol), bis-(tert-butyl-phosphine) palladium (67.5 mg, 0.13 mmol), and palladium acetate (7.4 mg, 0.003 mmol) in THF (10 mL) was added (2-tert-butoxy-2-oxoethyl)(chloro)zinc (6.6 mL, 3.3 mmol, 0.5 M in diethyl ether). The mixture was then heated to 50 C overnight, cooled to r.t. and quenched by addition of MeOH (1 mL). EtOAc was added and the solution was extracted with 5% KHSO4. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified on silica (gradient elution, 0-25% EtOAc/hexanes) to yield the title product (382 mg). HRMS (ESI) calc (M+H)+=367.1419. found 367.1422.

Provenance & Evidence