Hydrochloric Acid → [4-(5-Methylisoxazol-4-yl)phenyl]acetic acid

HRID 2383513Notes

Reaction equation

HRID 2383513 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=2)O1.I[C:21]1[CH:22]=[N:23][O:24][C:25]=1[CH3:26].CC1C(P(C2C(C)=CC(C)=C(S([O-])(=O)=O)C=2)C2C(C)=CC(C)=C(S([O-])(=O)=O)C=2)=CC(S([O-])(=O)=O)=C(C)C=1.[Na+].[Na+].[Na+].C(NC(C)C)(C)C.Cl>CC#N.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:26][C:25]1[O:24][N:23]=[CH:22][C:21]=1[C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:13][CH:14]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 27954614-Iodo-5-methylisoxazoleHCID 37190022-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic AcidHCID 11239198Txpts

Product 1

HCID 66893040[4-(5-Methylisoxazol-4-yl)phenyl]acetic acid

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.50 g (1.91 mmol) 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaboro-lan-2-yl)phenylacetic acid in 1.90 ml CH3CN and 1.90 ml water was added 0.48 g (2.29 mmol) 4-iodo-5-methyl-isoxazole, 0.08 g (0.12 mmol) TXPTS, 0.01 g (0.05 mmol) Palladium (II) acetate, and 0.54 mL (3.82 mmol) diisopropylamine. After 20 min in the microwave at 120° C., the reaction mixture was cooled, acidified to a pH of 1 with 1N HCl, extracted with CH2Cl2, and washed with brine. The organic layer was dried over NaSO4, filtered and concentrated in vacuo and afforded 0.57 g of ([4-(5-methylisoxazol-4-yl)phenyl]acetic acid that was used without further purification. 1H NMR (CDCl3, 400 MHz) 7.50-7.47 (m, 2H); 7.39-7.33 (m, 3H); 7.32-7.26 (m, 1H); 3.70 (s, 2H). Electrospray mass spec M+H=218.1.

Workup

  1. temperaturethe reaction mixture was cooled
  2. extractionextracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over NaSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b095b412aa6a40bab8e5d4bb1c1126f4
Source dataset
uspto-grants-2012_09
Patent number
US08263627B2

Reaction notes

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