Pyridine → Ethyl 3-(4-methoxyphenyl)-4-methyl-7-(pivaloyloxy)isoxazolo[4,5-c]pyridine-6-carboxylate

HRID 2388228Notes

Reaction equation

HRID 2388228 reaction equation
[OH:1][C:2]1[C:3]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[C:4]=2[C:5]([CH3:13])=[N:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].N1C=CC=CC=1.[C:31](Cl)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33].C(=O)(O)[O-].[Na+]>CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([C:14]2[C:4]3[C:5]([CH3:13])=[N:6][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:2]([O:1][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[C:3]=3[O:16][N:15]=2)=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 516892Sodium BicarbonateHCID 67530662HCID 67530662, compound

Product 1

HCID 67530063Ethyl 3-(4-methoxyphenyl)-4-methyl-7-(pivaloyloxy)isoxazolo[4,5-c]pyridine-6-carboxylateYield 82.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 7-hydroxy-3-(4-methoxyphenyl)-4-methylisoxazolo[4,5-c]pyridine-6-carboxylate (56 mg, 0.17 mmol) and DMAP (1 mg) were added to pyridine (1 mL). Pivaloyl chloride (84 μl, 0.68 mmol) was added and the mixture was stirred at room temperature for 48 h. Saturated sodium bicarbonate solution (5 mL) and EtOAc (15 mL) were added, and the aqueous layer was extracted with additional EtOAc. The combined organic layer was dried over MgSO4, concentrated, and the residue was purified by flash chromatography (0-20% EtOAc/hexanes) to give 58 mg of the title compound. MS: (+) m/z 413.50 (M+1).

Workup

  1. extractionthe aqueous layer was extracted with additional EtOAc
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customthe residue was purified by flash chromatography (0-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-32fa4da0b9be41c0a2cabd541d7d76e0
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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