Cesium carbonate → HCID 67530662, compound

HRID 2388220Notes

Reaction equation

HRID 2388220 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].[CH3:25]B(O)O.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]([CH3:25])=[N:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 139377Methylboronic AcidHCID 86648124Ethyl 7-hydroxy-4-iodo-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylate

Product 1

HCID 67530662HCID 67530662, compoundYield 16.7%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Ethyl 7-hydroxy-4-iodo-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylate (280 mg, 0.64 mmol), methylboronic acid (155 mg, 127 mmol), Pd(PPh3)4 (147 mg, 0.13 mmol) and cesium carbonate (622 mg, 1.91 mmol) were added to a flask and the flask evacuated. After refilling with nitrogen, 6.5 mL of 1,2-dimethoxyethane was added and the resulting suspension was refluxed for 16 h. The reaction mixture diluted with EtOAc (40 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 35 mg of the title compound. MS: (+) m/z 329.41 (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 (40 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-8f766fb311934b219cf0af3f25a38518
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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