Cesium carbonate → Ethyl 7-hydroxy-3-(4-methoxyphenyl)-4-phenylisoxazolo[4,5-c]pyridine-6-carboxylate

HRID 2388218Notes

Reaction equation

HRID 2388218 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](I)=[N:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 86648124Ethyl 7-hydroxy-4-iodo-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylate

Product 1

HCID 67531952Ethyl 7-hydroxy-3-(4-methoxyphenyl)-4-phenylisoxazolo[4,5-c]pyridine-6-carboxylateYield 38.7%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Ethyl 7-hydroxy-4-iodo-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylate (200 mg, 0.45 mmol), phenylboronic acid (111 mg, 0.91 mmol), Pd(PPh3)4 (105 mg, 0.091 mmol) and cesium carbonate (444 mg, 1.36 mmol) were added to a flask and the flask evacuated. After refilling with nitrogen, 3 mL of 1,2-dimethoxyethane was added and the resulting suspension was refluxed for 16 h. The reaction mixture diluted with EtOAc (50 mL) and the solid was filtered. The solid was added to a mixture of 10% hydrochloric acid and extracted several times with EtOAc. The combined organic layer was dried over MgSO4 and concentrated, and the residue was purified flash chromatography (0-40% EtOAc/hexanes) to afford 68 mg of the title compound. MS: (+) m/z 391.41 (M+1).

Workup

  1. customthe flask evacuated
  2. additionwas added
  3. temperaturethe resulting suspension was refluxed for 16 h
  4. additionThe reaction mixture diluted with EtOAc (50 mL)
  5. filtrationthe solid was filtered
  6. additionThe solid was added to a mixture of 10% hydrochloric acid
  7. extractionextracted several times with EtOAc
  8. dry with materialThe combined organic layer was dried over MgSO4
  9. concentrationconcentrated
  10. customthe residue was purified flash chromatography (0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-38bb04281bc24e5c8c4db53142de9818
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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