Water → HCID 21111440, compound

HRID 1627539Notes

Reaction equation

HRID 1627539 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][C:13]([NH2:30])=[C:14]([O:16][CH:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=3[C:26]([F:29])([F:28])[F:27])[CH3:18])[CH:15]=2)=[CH:6][CH:5]=1.O.[Li+].[OH-]>CC(O)C.CCOC(C)=O>[NH2:30][C:13]1[N:12]=[CH:11][C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:31])=[O:2])=[CH:5][CH:6]=2)=[CH:15][C:14]=1[O:16][CH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=1[C:26]([F:29])([F:28])[F:27])[CH3:18]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 58886089HCID 58886089, compound

Product 1

HCID 21111440HCID 21111440, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-{6-amino-5-[1-(3-fluoro-2-trifluoromethyl-phenyl)-ethoxy]-pyridin-3-yl}-benzoic acid methyl ester (1.4 g, 3.2 mmol) in warm IPA (72 mL) was added H2O (38 mL) containing LiOH (0.68 g, 16.2 mmol). The reaction was heated to reflux for 3.5 hr. The reaction was neutralized and diluted with EtOAc (200 mL) and extracted upon cooling. The organic layer was washed with brine (50 mL), dried over Na2SO4 and concentrated under vacuum to yield 4-{6-Amino-5-[1-(3-fluoro-2-trifluoromethyl-phenyl)-ethoxy]-pyridin-3-yl}-benzoic acid (1.2 g, 2.8 mmol, 88%). 1H NMR (MeOD, 300 MHz) δ 1.75 (d, 3H, J, 6.2 Hz), 4.88-4.93 (m, 1H), 7.01 (d, 1H, J, 1.8 Hz), 7.39 (d, 2H, J, 8.3 Hz), 7.52-7.67 (m, 3H), 7.80 (d, 1H, J, 1.8 Hz), 7.97 (d, 2H, J, 8.3 Hz).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3.5 hr
  3. extractionextracted
  4. temperatureupon cooling
  5. washThe organic layer was washed with brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f6c10ce5e86f4586a2fdf26288a9a3f6
Source dataset
uspto-grants-2014_07
Patent number
US08785632B2

Reaction notes

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