Sodium Bicarbonate → HCID 86669240, compound

Participants

Reaction Steps

1-Methylethyl[(2S,4R)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 52) (108 mg, 0.259 mmol), 2-bromo-1,3-thiazole-5-carbaldehyde (74.7 mg, 0.389 mmol), sodium bicarbonate (32.7 mg, 0.389 mmol) and tetrakis(triphenylphosphine)palladium(0) (30.0 mg, 0.026 mmol) were stirred at 100° C. in 1,2-dimethoxyethane (DME) (4 mL) under nitrogen for 16 h then cooled to room temperature. A saturated NaHCO3 aqueous solution (1 mL) was added and the resulting mixture was stirred at 100° C. for 4 h then cooled to room temperature and concentrated in vacuo. The residue was dissolved in DCM and the organic phase was filtered through celite then concentrated in vacuo to give 1-methylethyl [(2S,4R)-1-acetyl-6-(5-formyl-1,3-thiazol-2-yl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (104 mg, 0.259 mmol, 100%) which was used in the next step without further purification. LCMS (method G): Retention time 0.91 min, [M+H]+=402.0

Provenance & Evidence