Nitromethane → HCID 178501788, compound

HRID 1394457Notes

Reaction equation

HRID 1394457 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:15]=[N:14][C:13](N2C=CC(C)=N2)=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2.Cl[C:23]([C:25]([O:27][CH3:28])=[O:26])=[O:24].[CH3:29][N+:30]([O-])=O>C(Cl)Cl>[CH3:28][O:27][C:25](=[O:26])[C:23]([C:9]1[C:8]2[C:12](=[C:13]([C:29]3[NH:30][N:11]=[C:12]([CH3:13])[CH:8]=3)[N:14]=[CH:15][C:7]=2[O:6][CH3:5])[NH:11][CH:10]=1)=[O:24]

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 79846Methyl chloroglyoxylateHCID 6451240Aluminum(III) ChlorideHCID 59681741HCID 59681741, compound

Product 1

HCID 178501788HCID 178501788, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of AlCl3 (0.411 g, 3.08 mmol) in CH2Cl2 (1.6 mL) and MeNO2 (0.4 mL) was added 4-methoxy-7-(5-methylpyrazol-2-yl)-6-azaindole (0.054 g, 0.237 mmol) as a solid. After dissolution of the starting material (ca. 5 min) ClCOCO2Me (0.087 mL, 0.946 mmol) was added and the mixture was allowed to stir for 5 h. The reaction was cooled to 0° C., quenched by the slow addition of 1 M aqueous NH4OAc and extracted with EtOAc (×3). The combined organic layers were washed (H2O, brine), dried (Na2SO4) and concentrated to give 4-methoxy-7-(3-methylpyrazol-5-yl)-6-azaindol-3-yl-oxoacetic acid methyl ester (0.0550 g, 75%): LCMS: m/e 315 (M+H)+. This material was dissolved in MeOH (2 mL) and treated with 2.5 M NaOH (0.14 mL, 0.35 mmol). The resulting mixture was allowed to stir for 1 h, at which point the solvent was removed and the residue diluted with H2O (2 mL). This mixture was acidified to pH 1 with 6 M HCl, the mixture was washed with EtOAc and then it was lyophilized to give the title compound (0.050 g), which contained a nominal amount of inorganic salts. This material was used as such in the following step:

Workup

  1. additionwas added
  2. customquenched by the slow addition of 1 M aqueous NH4OAc
  3. extractionextracted with EtOAc (×3)
  4. washThe combined organic layers were washed (H2O, brine)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-069d88c2f59d4096b5c764cfa02e79c4
Source dataset
uspto-grants-2008_03
Patent number
US07348337B2

Reaction notes

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