5-Methyl-3-phenylisoxazole-4-carboxylic acid → 4-(5-Methyl-3-phenyl-isoxazole-4-carbonyl)-1H-pyrrole-2-carboxylic acid methyl ester

HRID 494316Notes

Reaction equation

HRID 494316 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([OH:15])=O.O=S(Cl)Cl.[CH3:20][O:21][C:22]([C:24]1[NH:25][CH:26]=[CH:27][CH:28]=1)=[O:23]>ClC(Cl)C>[CH3:20][O:21][C:22]([C:24]1[NH:25][CH:26]=[C:27]([C:13]([C:3]2[C:4]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:5][O:6][C:2]=2[CH3:1])=[O:15])[CH:28]=1)=[O:23]

Participants

5

Reactant 3

HCID 143435-Methyl-3-phenylisoxazole-4-carboxylic acidHCID 24386Thionyl ChlorideHCID 136930Methyl pyrrole-2-carboxylate

Product 1

HCID 576831324-(5-Methyl-3-phenyl-isoxazole-4-carbonyl)-1H-pyrrole-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 406 mg (2 mmol) 5-methyl-3-phenyl-isoxazole-4-carboxylic acid (commercially available) and 4 mL SOCl2 was heated to reflux for 3 h. After evaporation of all volatiles the residue was added to a mixture of 206 mg (2 mmol) 1H-pyrrole-2-carboxylic acid methyl ester (commercially available) and 440 mg (3 mmol) AMCl3 in 25 mL dichloroethane and heated to reflux for 3 h. After cooling to room temperature the precipitate was collected and washed with dichloromethane. The residue was purified on silica eluting with a gradient of ethyl acetate and heptane affording 210 mg (37%) of the title compound as white foam. (m/e): 311.0 (MH+; 100%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. customAfter evaporation of all volatiles the residue
  4. temperatureto reflux for 3 h
  5. customwas collected
  6. washwashed with dichloromethane
  7. customThe residue was purified on silica eluting with a gradient of ethyl acetate and heptane affording 210 mg (37%) of the title compound as white foam

Sources & evidence

ORD record
ord-7511680f8a5049378033178ec0310b4c
Source dataset
uspto-grants-2009_05
Patent number
US07538132B2

Reaction notes

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