6-Bromopyridine-2-carbaldehyde → HCID 86663391, compound

Participants

Reaction Steps

A solution of 37.0 g (129 mmol) of Na2CO3(H2O)10 in a mixture of 200 ml of methanol and 600 ml of water was added to a mixture of 9.58 g (51.5 mmol) of 6-bromopyridine-2-carbaldehyde, 17.5 g (51.5 mmol) of tert-butyl{[1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}amine and 3.00 g (2.60 mmol) of Pd(PPh3)4 in 1000 ml of toluene by vigorous stirring at room temperature. The resulting mixture was stirred at 80° C. for 12 h. Further on, this mixture was cooled to room temperature; the organic layer was separated and evaporated to dryness. The residue was dissolved in 700 ml of 2 M HCl, and this solution was extracted with 3×200 ml of toluene. To the aqueous layer a solution of K2CO3 was added to pH 9, and the product was extracted with 2×300 ml of dichloromethane. This organic extract was dried over MgSO4 and then evaporated to dryness. Yield 15.2 g (46%). Anal. calc. for C21H22N2O: C, 79.21; H, 6.96; N, 8.80. Found: C, 79.30; H, 7.14; N, 8.65. 1H NMR (CDCl3): 10.18 (s, 1H, CHO), 8.07 (m, 1H, 3-H in Py), 8.02 (m, 1H, 4-H in Py), 7.92 (m, 1H, 8-H in naphthyl), 7.88 (m, 1H, 5-H in naphthyl), 7.71 (m, 1H, 5-H in Py), 7.66 (d, J=8.3 Hz, 1H, 4-H in naphthyl), 7.45 (m, 1H, 7-H in naphthyl), 7.36 (m, 1H, 6-H in naphthyl), 7.28 (d, J=8.3 Hz, 1H, 3-H in naphthyl), 3.53 (m, 2H, CH2N), 1.55 (br. s, 1H, NH), 0.94 (s, 9H, tBu).

Provenance & Evidence