Potassium Carbonate → HCID 86301019, compound

HRID 513932Notes

Reaction equation

HRID 513932 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:19]=[C:18]3[C:13]([CH:14]=[C:15]([C:20]([O:22][CH2:23]C)=[O:21])[CH:16]=[N:17]3)=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CO.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([C:20]([O:22][CH3:23])=[O:21])[CH:16]=[N:17]2)=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86296057HCID 86296057, compound

Product 1

HCID 86301019HCID 86301019, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 7-[(3-chlorophenyl)methoxy]quinoline-3-carboxylate (Example 3, 20 mg, 0.06 mmol) in MeOH (1 mL) and THF (1 mL) was added K2CO3. The reaction was stirred overnight at ambient temperature. The crude reaction mixture was concentrated onto silica and purification (FCC, SiO2, 0-40%, EtOAc/hexanes) afforded the title compound as a white solid (12 mg, 63%). 1H NMR (400 MHz, CDCl3) δ 9.37 (d, J=2.0 Hz, 1H), 8.76 (d, J=2.3 Hz, 1H), 7.84 (d, J=9.0 Hz, 1H), 7.50 (d, J=2.3 Hz, 2H), 7.38-7.30 (m, 4H), 5.21 (s, 2H), 4.00 (s, 3H). [M+H]=328.2.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated onto silica and purification (FCC, SiO2, 0-40%, EtOAc/hexanes)

Sources & evidence

ORD record
ord-cad7a0f8322a4668bbfd03bad743b553
Source dataset
uspto-grants-2015_08
Patent number
US09102674B2

Reaction notes

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