Tetrahydrofuran → HCID 67083692, compound

HRID 79041Notes

Reaction equation

HRID 79041 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:9]([O:13][C:14]([N:16]1[C:24]2[C:19](=[C:20]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([I:35])=[CH:31][C:30]=3[F:36])[C:21]([N+:25]([O-])=O)=[CH:22][CH:23]=2)[CH:18]=[N:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C1COCC1.C(=O)([O-])O.[Na+]>O.O1CCOCC1>[C:9]([O:13][C:14]([N:16]1[C:24]2[C:19](=[C:20]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([I:35])=[CH:31][C:30]=3[F:36])[C:21]([NH2:25])=[CH:22][CH:23]=2)[CH:18]=[N:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24489Sodium Dithionite2×HCID 516892Sodium BicarbonateHCID 67083679HCID 67083679, compound

Product 1

HCID 67083692HCID 67083692, compoundYield 115.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of sodium dithionite (978 mg, 4.21 mmol) and 4-(2-fluoro-4-iodo-phenylamino)-5-nitro-indazole-1-carboxylic acid tert-butyl ester (700 mg, 1.4 mmol) in water (35 mL) was treated with a 1:1 mixture of THF:dioxane (34 mL), the homogeneous reaction mixture stirred at room temperature for 4 hours. Further sodium dithionite (978 mg, 4.21 mmol) was added and stirring continued for 20 hours. The reaction mixture was basified by the addition of saturated aqueous sodium hydrogen carbonate and then extracted with ethyl acetate (150 mL). The organic extract was washed with water, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a yellow solid (758 mg, quant.). LCMS (Method B) RT=4.09 min, [M+H]+=469.

Workup

  1. extractionextracted with ethyl acetate (150 mL)
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bdf00e9c514b48ef86e3aa29408ecc2c
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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