Sodium Carbonate → HCID 11655212, compound

Reaction equation

[C:1](=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[C:9]([C:21]#[C:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][CH:35]([CH3:38])[CH2:34][CH2:33]3)=[CH:25][CH:24]=2)=[N:10][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH:13]=1.COB(O)O>O1CCOCC1>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[CH:13]=[C:8]([CH3:1])[C:9]([C:21]#[C:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]4[CH2:37][CH2:36][CH:35]([CH3:38])[CH2:34][CH2:33]4)=[CH:25][CH:24]=3)=[N:10][CH:11]=2)=[CH:15][CH:16]=1

Participants

Procedure

2.5 n-L of 2M aqueous sodium carbonate solution and 15 mg (0.013 mmol) of tetrakis(triphenylphosphane)palladium were added under argon to a suspension of 130 mg (0.255 mmol) of 3-bromo-5-(4-chlorophenyl)-2-{4-[2-(4-methylpiperidin-1-yl)ethoxy]phenylethynyl}pyridine and 18.9 mg (0.306 mmol) of methylboric acid in 5 mL of 1,4-dioxane and the mixture was refluxed for 5 hours. A further 18.9 mg (0.306 mmol) of methylboric acid was added and again the mixture was refluxed for 2 hours. The reaction mixture was exhaustively extracted with EtOAc, the combined organic phases were washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, and evaporated down in vacuo. The residue was purified by HPLC-MS (Symmetry C18, gradient 0.15% formic acid in water/acetonitrile 10/90→50/50 v/v) and the product fractions were lyophilized. Product fraction 1: Yield: 12 mg (11% of theoretical); C28H29ClN2O (M=444.995); calc.: molpeak (M+H)+: 445/447 (Cl); found: molpeak (M+H)+: 445/447 (Cl); HPLC-MS: 4.00 minutes (method E).