Tetrahydrofuran → HCID 67083628, compound

HRID 79047Notes

Reaction equation

HRID 79047 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:30][C:31]3[CH:36]=[CH:35][C:34]([I:37])=[CH:33][C:32]=3[F:38])[C:21]([N+:27]([O-])=O)=[C:22]([O:25][CH3:26])[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:30][C:31]3[CH:36]=[CH:35][C:34]([I:37])=[CH:33][C:32]=3[F:38])[C:21]([NH2:27])=[C:22]([O:25][CH3:26])[CH:23]=2)[CH:18]=[N:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 67083725HCID 67083725, compound

Product 1

HCID 67083628HCID 67083628, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of sodium dithionite (524 mg, 3.48 mmol) and 4-(2-fluoro-4-iodo-phenylamino)-6-methoxy-5-nitro-indazole-1-carboxylic acid tert-butyl ester (434 mg, 0.87 mmol) in water (10 mL) was treated with a 1:1 mixture of THF:dioxane (10 mL). The homogeneous reaction mixture stirred at room temperature for 18 hours. The reaction mixture was basified by the addition of saturated aqueous sodium hydrogen carbonate and then extracted twice with ethyl acetate. The combined organic extracts were washed with water, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a yellow solid (300 mg, 73%). LCMS (Method B) RT 4.16 min, [M+H]+=499 [M−H]−=497.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c82cdce92fe84cd1b56538f6784ef1b0
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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