Sodium Carbonate → HCID 15453754, compound

HRID 2230778Notes

Reaction equation

HRID 2230778 reaction equation
Br[C:2]1[N:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:12]([C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)#[N:13].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:12]([C:14]1[CH:19]=[C:18]([C:2]2[N:11]=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])[CH:17]=[CH:16][CH:15]=1)#[N:13]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 12349191Methyl 2-bromopyridine-3-carboxylate

Product 1

HCID 15453754HCID 15453754, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 241BenzeneSolvent

Procedure

Methyl 2-bromonicotinate (2.0 g, 9.3 mmol) and 3-cyanophenylboronic acid (2.7 g, 18.4 mmol) were combined in 190 mL benzene. Sodium carbonate (19 mL of a 2 M aqueous solution), tetrabutylammonium bromide (152 mg, 0.5 mmol), and bis(triphenylphosphine)palladium(II) chloride (325 mg, 0.5 mmol) were added. The entire mixture was evacuated to remove dissolved gasses, then placed under argon. The reaction was refluxed for 14 hours, diluted with water and EtOAc, separated, dried over Na2SO4, filtered, and evaporated. The resulting yellow solid was chromatographed on silica gel (30% EtOAc/hexanes) to yield a light yellow solid (1.70 g, 77%). 1H NMR (CDCl3): δ8.81 (dd, 1H, J=4.8, J′=1.8), 8.23 (dd, 1H, J=8.0, J′=1.9), 7.85 (s, 1H), 7.73 (m, 2H), 7.55 (t, 1H, J=7.7), 7.43 (m, 1H), 3.76 (s, 3H).

Workup

  1. customThe entire mixture was evacuated
  2. customto remove
  3. dissolutiondissolved gasses
  4. temperatureThe reaction was refluxed for 14 hours
  5. additiondiluted with water and EtOAc
  6. customseparated
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe resulting yellow solid was chromatographed on silica gel (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8ab48df4f45147b090c7f7a74d9ea4aa
Source dataset
uspto-grants-2002_07
Patent number
US06426346B1

Reaction notes

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