Sodium Hydroxide → 5-(5-(Tert-butoxycarbonyl)-2-methylphenyl)-2-(4-fluorophenyl)furo[2,3-b]pyridine-3-carboxylic acid

HRID 219412Notes

Reaction equation

HRID 219412 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]([CH3:36])=[C:14]([C:16]2[CH:17]=[C:18]3[C:24]([C:25]([O:27]C)=[O:26])=[C:23]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)[O:22][C:19]3=[N:20][CH:21]=2)[CH:15]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO.C1COCC1.CCOC(C)=O>[C:3]([O:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]([CH3:36])=[C:14]([C:16]2[CH:17]=[C:18]3[C:24]([C:25]([OH:27])=[O:26])=[C:23]([C:29]4[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=4)[O:22][C:19]3=[N:20][CH:21]=2)[CH:15]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67217142HCID 67217142, compound

Product 1

HCID 674056235-(5-(Tert-butoxycarbonyl)-2-methylphenyl)-2-(4-fluorophenyl)furo[2,3-b]pyridine-3-carboxylic acidYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaOH (1.4 mL, 1.37 mmol) was added to a stirring solution of methyl 5-(5-(tert-butoxycarbonyl)-2-methylphenyl)-2-(4-fluorophenyl)furo[2,3-b]pyridine-3-carboxylate (211 mg, 0.457 mmol) in MeOH (2.3 mL) and THF (2.3 mL) at 60° C. It was allowed to stir for 4 hours. The mixture was diluted with EtOAc and washed with 1M HCl, and sat NaCl. The organic phase was dried over Na2SO4, filtered and concentrated to give the expected product 5-(5-(tert-butoxycarbonyl)-2-methylphenyl)-2-(4-fluorophenyl)furo[2,3-b]pyridine-3-carboxylic acid (205 mg, 0.457 mmol, quant.) consistent by LCMS crude which was used directly in the next step. LC-MS retention time: 1.88 min; m/z (MH+): 448. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters XBridge 5u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 5% MeOH/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% MeOH/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode.

Workup

  1. washwashed with 1M HCl
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-930ba1c1b7b0485fb20dc496698f03c4
Source dataset
uspto-grants-2012_06
Patent number
US08198449B2

Reaction notes

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