Sodium Carbonate → HCID 58438484, compound

HRID 1913405Notes

Reaction equation

HRID 1913405 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[CH2:13][CH2:12]3)O1.Cl[C:21]1[N:26]=[CH:25][C:24]([CH3:27])=[CH:23][N:22]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].O>[CH3:27][C:24]1[CH:23]=[N:22][C:21]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[CH2:13][CH2:12]3)=[N:26][CH:25]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 5817192-Chloro-5-methylpyrimidineHCID 185417105-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-one

Product 1

HCID 58438484HCID 58438484, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

To a 100 mL round-bottomed flask was added 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indan-1-one (SM-1a, 1.50 g, 5.81 mmol), 2-chloro-5-methylpyrimidine (747 mg, 5.81 mmol), sodium carbonate (2.47 g, 23.3 mmol), 27 mL of dioxane, and 3 mL of water. The mixture was degassed with nitrogen for 15 minutes. Palladium tetrakis(triphenylphosphine) (356 mg, 0.31 mmol) was added and the mixture was degassed with nitrogen for an additional 15 minutes. The reaction was heated at reflux overnight. The reaction was cooled to room temperature and was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The final product was purified by silica chromatography on a Combiflash ISCO purification system (Teledyne Isco Inc., Lincoln, Nebr.) eluting with 20-35% ethyl acetate in heptanes to provide a white solid (SM-1d, 1.12 g, 86%). MS (ES+) 225.2 (M+H+). 1H NMR (CDCl3) δ 2.38 (s, 3H), 2.74-2.78 (m, 2H), 3.23 (t, 2H), 7.85 (d, 1H), 8.44 (d, 1H), 8.53 (s, 1H), 8.68 (s, 2H).

Workup

  1. customThe mixture was degassed with nitrogen for 15 minutes
  2. customthe mixture was degassed with nitrogen for an additional 15 minutes
  3. temperatureThe reaction was heated
  4. temperatureat reflux overnight
  5. customwas partitioned between ethyl acetate and water
  6. extractionThe aqueous layer was extracted with ethyl acetate (2×)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe final product was purified by silica chromatography on a Combiflash ISCO purification system (Teledyne Isco Inc., Lincoln, Nebr.)
  12. washeluting with 20-35% ethyl acetate in heptanes
  13. customto provide a white solid (SM-1d, 1.12 g, 86%)

Sources & evidence

ORD record
ord-adba6b37077a4cd39c0045617b64faf2
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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