Tert-butyl 2-hydroxyacetate → [5-(4-Fluoro-phenylcarbamoyl)-pyridin-2-yloxy]-acetic acid tert-butyl ester

HRID 1836443Notes

Reaction equation

HRID 1836443 reaction equation
Br[C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[C:18]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:21])[CH2:19][OH:20].CC(C)([O-])C.[K+]>C1COCC1.C(OCC)(=O)C>[C:23]([O:22][C:18](=[O:21])[CH2:19][O:20][C:2]1[CH:17]=[CH:16][C:5]([C:6](=[O:7])[NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[CH:4][N:3]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 11815394Tert-butyl 2-hydroxyacetateHCID 218782716-Bromo-N-(4-Fluorophenyl)NicotinamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 15980917[5-(4-Fluoro-phenylcarbamoyl)-pyridin-2-yloxy]-acetic acid tert-butyl esterYield 8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 6-bromo-N-(4-fluoro-phenyl)-nicotinamide (0.112 g, 0.38 mmol), tert-butyl glycolate (0.1 g, 0.76 mmol), and potassium tert-butoxide (0.85 g, 0.76 mmol) in THF (10 mL) was heated in a sealed tube at 70° C. After 6 h the reaction mixture was diluted with ethyl acetate and washed with water bicarbonate and dried over sodium sulfate. Removal of the solvents provided a solid. Purification by reverse phase chromatography gave 0.010 g (8%) of the titled product as a white solid; MS (EI) m/z 345.21 (M−H)−.

Workup

  1. washwashed with water bicarbonate
  2. dry with materialdried over sodium sulfate
  3. customRemoval of the solvents
  4. customprovided a solid
  5. customPurification by reverse phase chromatography

Sources & evidence

ORD record
ord-9f94807a17774055923938e6d263eea7
Source dataset
uspto-grants-2004_08
Patent number
US06777432B1

Reaction notes

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