Potassium Carbonate → HCID 86296848, compound

HRID 513953Notes

Reaction equation

HRID 513953 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([CH2:17][C:18]([O:20][CH2:21]C)=[O:19])[CH:13]=[N:14]2)=[CH:9][CH:8]=1.C([O-])([O-])=O.[K+].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:13]=[N:14]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86296662HCID 86296662, compound

Product 1

HCID 86296848HCID 86296848, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-(7-((3-chlorobenzyl)oxy)quinolin-3-yl)acetate (Example 51, 50 mg, 0.14 mmol) in MeOH (3.0 mL) was added K2CO3 (50 mg, 0.36 mmol). The reaction was stirred at ambient temperature for 30 minutes. The reaction was loaded directly onto the column and purification (FCC, SiO2, 0-50%, EtOAc/hexanes) afforded the title compound as a white solid (33 mg, 69%). 1H NMR (400 MHz, CDCl3) δ 8.75 (d, J=2.0 Hz, 1H), 8.01 (s, 1H), 7.71 (d, J=9.0 Hz, 1H), 7.49 (s, 1H), 7.45 (d, J=2.7 Hz, 1H), 7.38-7.27 (m, 4H), 5.19 (s, 2H), 3.79 (s, 2H), 3.73 (s, 3H). [M+H]=342.2.

Workup

  1. customThe reaction was loaded directly onto the column and purification (FCC, SiO2, 0-50%, EtOAc/hexanes)

Sources & evidence

ORD record
ord-e9e466d1d02543dcbf4a3aa6c98e12e6
Source dataset
uspto-grants-2015_08
Patent number
US09102674B2

Reaction notes

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