Potassium Carbonate → HCID 11960947, compound

Participants

Reaction Steps

Treatment of (±)-(5-chloro-7-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (1.37 g, 2.81 mmol) with 2-methylphenylboronic acid (0.65 g, 4.60 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.25 g, 0.30 mmol), and potassium carbonate (0.83 g, 6.0 mmol) generally according to the procedure described for Intermediate 35 provided (±)-[5-chloro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate. Treatment of the tosylate with sodium azide (1.04 g, 16.1 mmol) generally according to the procedure described for Intermediate 98 provided (±)-2-(azidomethyl)-5-chloro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with sulfided platinum on carbon (200 mg, 5 wt. %) generally according to the procedure described for Example 1 gave 0.70 g (80%) of (±)-1-[5-chloro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a light yellow solid, hydrochloric salt. mp 160-163° C.; Anal. calcd. for C16H16ClNOHCl: C, 61.95; H, 5.52; N, 4.52. Found: C, 57.75; H, 5.4; N, 3.95.

Provenance & Evidence