Ethyl Acetate → HCID 66767128, compound

HRID 2195500Notes

Reaction equation

HRID 2195500 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([N+:29]([O-])=O)[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14]1[CH:15]=[N:16][NH:17][CH:18]=1)[N:10](C1CCCCO1)[N:9]=[CH:8]2.C(OC(N1C=C(C2C=C3C(C=NN3C3CCCCO3)=CC=2OC2C=CC([N+]([O-])=O)=CC=2F)C=N1)=O)(C)(C)C.C([O-])(O)=O.[Na+].CCOC(C)=O>CCOC(C)=O.CCO>[NH:16]1[CH:15]=[C:14]([C:13]2[CH:12]=[C:11]3[C:7]([CH:8]=[N:9][NH:10]3)=[CH:6][C:5]=2[O:4][C:3]2[CH:25]=[CH:26][C:27]([NH2:29])=[CH:28][C:2]=2[F:1])[CH:18]=[N:17]1

Participants

6

Reactant 4

HCID 8857Ethyl Acetate2×HCID 516892Sodium BicarbonateHCID 66767109HCID 66767109, compoundHCID 66767154HCID 66767154, compound

Product 1

HCID 66767128HCID 66767128, compoundYield 265.6%

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of 5-(2-fluoro-4-nitrophenoxy)-6-(1H-pyrazol-4-yl)-1-(tetrahydropyran-2-yl)-1H-indazole (900 mg, 2.13 mmol) and 4-[5-(2-fluoro-4-nitro-phenoxy)-1-(tetrahydropyran-2-yl)-1H-indazol-6-yl]-pyrazole-1-carboxylic acid tert-butyl ester (3.1 g, 5.92 mmol) in EtOAc/EtOH (75 mL/75 mL) is added stannous chloride dihydrate (10 g, 52.74 mmol). The reaction mixture is stirred at reflux overnight. After it is cooled and basified with saturated aqueous NaHCO3 to pH 8-9, the mixture is extracted with EtOAc (100 mL). The organic phase is separated, dried over MgSO4, and concentrated. The residue is purified by silica gel column chromatography eluting first with PE:EtOAc (1:1) and then with EtOAc to give the product (1.75 g, 71.0% yield). MS (m/z): 310.0 (M+H).

Workup

  1. temperatureat reflux overnight
  2. temperatureAfter it is cooled
  3. extractionthe mixture is extracted with EtOAc (100 mL)
  4. customThe organic phase is separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel column chromatography
  8. washeluting first with PE

Sources & evidence

ORD record
ord-6764eda73c7a4fd4b2d72640d8bac81f
Source dataset
uspto-grants-2012_12
Patent number
USRE043878E1

Reaction notes

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