Sodium Carbonate → HCID 11655212, compound

HRID 734820Notes

Reaction equation

HRID 734820 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

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11598674HCID 11598674, compoundHCID 14178740Methylborat2×

Product 1

HCID 11655212HCID 11655212, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. temperatureagain the mixture was refluxed for 2 hours
  3. extractionThe reaction mixture was exhaustively extracted with EtOAc
  4. washthe combined organic phases were washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated down in vacuo
  7. customThe residue was purified by HPLC-MS (Symmetry C18, gradient 0.15% formic acid in water/acetonitrile 10/90→50/50 v/v)
  8. custom4.00 minutes (method E)

Sources & evidence

ORD record
ord-88646192cdb94c31887cb84a8acde73f
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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