Potassium Carbonate → HCID 86301019, compound

HRID 1748382Notes

Reaction equation

HRID 1748382 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-805d628bc2b84fb0a1878ca636753809
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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