Potassium tert-butoxide → 6-[4-({[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid potassium salt

HRID 2423390Notes

Reaction equation

HRID 2423390 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[N:28]=[C:27]([C:32]([OH:34])=[O:33])[CH:26]=[CH:25]4)=[CH:18][CH:17]=2)=[C:12]([CH:35]([CH3:37])[CH3:36])[O:11][N:10]=1.CC(C)([O-])C.[K+:43]>C(O)C.C(O)(C)(C)C>[K+:43].[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[N:28]=[C:27]([C:32]([O-:34])=[O:33])[CH:26]=[CH:25]4)=[CH:18][CH:17]=2)=[C:12]([CH:35]([CH3:37])[CH3:36])[O:11][N:10]=1

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 247719836-(4-{[3-(2,6-Dichlorophenyl)-5-(1-Methylethyl)isoxazol-4-Yl]methoxy}phenyl)quinoline-2-Carboxylic Acid

Product 1

HCID 248241296-[4-({[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid potassium saltYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6386tert-ButanolSolvent

Procedure

A stirred suspension of 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid (179 g, 0.335 mol) in ethanol (2.6 L) was treated with 1 N potassium tert-butoxide in tert-butyl alcohol (350 mL) and stirred at room temperature under N2 for 1 hour. The mixture was then heated to a gentle reflux for 2 hours and was stirred overnight at room temperature. The suspension was filtered, then the filter cake was washed with hexane, combined with 5 g of similarly prepared material and dried at 60° C. in a vacuum oven overnight to yield 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid potassium salt as a beige solid (181 g, 84%). 1H NMR (400 MHz, DMSO-d6): 8.25 (d, J=9 Hz, 1H), 8.18 (d, J=9 Hz, 1H), 8.08 (d, J=2 Hz, 1H), 8.02 (d, J=8 Hz, 1H), 7.94 (dd, J=2, 9 Hz, 1H), 7.68 (d, J=9 Hz, 2H), 7.62 (d, J=8 Hz, 2H), 7.53 (dd, J=7, 9 Hz, 1H), 6.90 (d, J=9 Hz, 2H), 4.86 (s, 2H), 3.46 (m, 1H), 1.32 (d, J=7 Hz, 6H). ES-LCMS m/z 533 (M+H)+.

Workup

  1. temperatureThe mixture was then heated to
  2. temperaturea gentle reflux for 2 hours
  3. stirringwas stirred overnight at room temperature
  4. filtrationThe suspension was filtered
  5. washthe filter cake was washed with hexane
  6. customdried at 60° C. in a vacuum oven overnight

Sources & evidence

ORD record
ord-ee210e02b59e474d917e478ca7fa9fb0
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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