Toluene → HCID 178488613, compound

HRID 1351995Notes

Reaction equation

HRID 1351995 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][N:9]=[C:8]2[CH2:12][CH2:13]C(O)=O.C([N:19](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:41](=[O:44])([O-])[OH:42].[Na+].[C:46]1([CH3:52])[CH:51]=CC=C[CH:47]=1>C(O)(C)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][N:9]=[C:8]2[CH2:12][CH2:13][NH:19][C:41](=[O:44])[O:42][C:46]([CH3:52])([CH3:51])[CH3:47]

Participants

7

Reactant 5

HCID 1140TolueneHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 178488589HCID 178488589, compound

Product 1

HCID 178488613HCID 178488613, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Under nitrogen atmosphere, to a solution of 3-(7-methoxy-1H-indazol-3-yl)propanoic acid (86.4 mg, 0.392 mmol) in toluene (5 mL)-tert-butanol (2.5 mL) are added triethylamine (80.0 μL, 0.574 mmol) and diphenylphosphoryl azide (110 μL, 0.510 mmol), and the mixture is stirred at room temperature for 2 hours. The mixture is stirred at 60° C. for 1 hour, and further stirred at 100° C. for 5 hours. The mixture is allowed to cool to room temperature, and thereto is added a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with ethyl acetate. The organic layer is dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. The obtained residue is purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1) to give the title compound (94.3 mg, yield: 82%).

Workup

  1. stirringThe mixture is stirred at 60° C. for 1 hour
  2. stirringfurther stirred at 100° C. for 5 hours
  3. temperatureto cool to room temperature
  4. extractionthe mixture is extracted with ethyl acetate
  5. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  6. customthe solvent is evaporated under reduced pressure
  7. customThe obtained residue is purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-3787d61b65d84468be7f7d5bd5b7ccfe
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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