Sodium Carbonate → HCID 22285307, compound

HRID 1061838Notes

Reaction equation

HRID 1061838 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[Cl:12])[N:3]=1.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[Cl:12][C:8]1[CH:7]=[CH:6][N:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[F:13])=[N:3]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 155883162,5-Dichloro-1,8-naphthyridine

Product 1

HCID 22285307HCID 22285307, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A stirred mixture of 2,5-dichloro-[1,8]naphthyridine (Barlin, G. B.; Tan, W.-L. Aust. J. Chem. 1984, 37, 1065) (0.1029 g, 0.513 mmol) and 2-fluorobenzeneboronic acid (72.4 mg, 0.517 mmol) in 2 N aqueous sodium carbonate (0.620 mL, 1.24 mmol) and ethylene glycol dimethyl ether (3 mL) was degassed by bubbling nitrogen through for 15 min. Tetrakis-(triphenylphosphine)palladium(0) (29.9 mg, 0.0259 mmol) was added and the mixture was degassed for a further 10 min, then heated at 80° C. for 16 h under nitrogen. The mixture was partitioned between water (20 mL) and dichloromethane (20 mL). The aqueous layer was further extracted with dichloromethane (2×20 mL), and the combined organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with 15% EtOAc/CH2Cl2, to afford 0.1216 g (91%) of the title compound as an off-white solid. δH (360 MHz, CDCl3) 7.22 (1H, dd, J 11.8 and 8.2), 7.34 (1H, td, J 7.7, 0.7), 7.49 (1H, tdd, J 7.4, 5.3, and 2.1), 7.58 (1H, d, J 4.7), 8.18 (1H, dd, J 8.8, 2.5), 8.39 (1H, td, J 7.7, 1.8), 8.66 (1H, d, J 8.8), 9.03 (1H, d, J 4.8).

Workup

  1. customwas degassed
  2. customby bubbling nitrogen through for 15 min
  3. customthe mixture was degassed for a further 10 min
  4. customThe mixture was partitioned between water (20 mL) and dichloromethane (20 mL)
  5. extractionThe aqueous layer was further extracted with dichloromethane (2×20 mL)
  6. dry with materialthe combined organic extracts were dried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel
  9. washeluting with 15% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-513842b2baa34ca5b0d91f9f55099174
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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