Potassium Carbonate → HCID 58318635, compound

HRID 473411Notes

Reaction equation

HRID 473411 reaction equation
Cl[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[N:3]=1.[CH2:18]([Zn]CC)[CH3:19].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH2:18]([C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[N:3]=1)[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59380854HCID 59380854, compound2×HCID 178418750HCID 178418750, compound

Product 1

HCID 58318635HCID 58318635, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-3-phenyl-1,5-naphthyridine was made according to a known procedure (WO 2005/100356). A mixture of 2-chloro-3-phenyl-1,5-naphthyridine (200 mg, 0.85 mmol), diethylzinc (0.87 mL, 1 M in hexane, 1.02 eq), K2CO3 (354 mg, 3.0 eq) and PdCl2(dppf)2 DCM complex (62.5 mg, 0.1 eq) in THF (5 mL) was purged with N2 for 5 min before heating to reflux. After 6 h, the reaction was quenched with NH4Cl and extracted with EtOAc and the residue was purified by silica gel column chromatography using hexane/DCM (2/3) as eluent to give a yellow solid. LC-MS (ESI) m/z 235 [M+H]+.

Workup

  1. customwas purged with N2 for 5 min
  2. temperaturebefore heating to reflux
  3. customthe reaction was quenched with NH4Cl
  4. extractionextracted with EtOAc
  5. customthe residue was purified by silica gel column chromatography
  6. customto give a yellow solid

Sources & evidence

ORD record
ord-c3bebb90cf81446b866bb63b32d4492f
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

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