2-Methoxyethanol → HCID 67347508, compound

Participants

Reaction Conditions

Reaction Steps

A round-bottomed flask was charged with 4-(methoxycarbonyl)phenylboronic acid (4.95 g, 27.5 mmol), 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)aniline (Example 6, Step A, 7.08 g, 18.3 mmol), cesium carbonate (8.96 g, 27.5 mmol) and 2-methoxyethanol (1.40 g, 18.3 mmol) (100 mL). The mixture was purged with nitrogen for 10 minutes and then Pd(PPh3)4 (1.27 g, 1.10 mmol) was added as a solid. The mixture was heated under nitrogen to 90° C. for 48 hours and then cooled to room temperature. NaOH (10 mL, 5N) was added and the mixture was stirred for 2 hours. The mixture was extracted with EtOAc (2×300 mL). The aqueous phase was acidified with HCl (2N) to pH 7. The formed precipitate was collected by filtration and washed with water to get the product (7.6 g, 109%, contains residual water) as a beige solid. LRMS (esi+) 381 m/z (M+1) detected.

Provenance & Evidence