Methanol → HCID 57901846, compound

HRID 1851557Notes

Reaction equation

HRID 1851557 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH:11][S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:14])=[O:13])[CH:10]=1)[NH:7][C:6]([C:20]([O:22]CC)=[O:21])=[CH:5]2.CO.[OH-].[K+]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH:11][S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:14])=[O:13])[CH:10]=1)[NH:7][C:6]([C:20]([OH:22])=[O:21])=[CH:5]2

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 57901584HCID 57901584, compound

Product 1

HCID 57901846HCID 57901846, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of ethyl 5-fluoro-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate (0.24 g) in tetrahydrofuran (10 mL)-methanol (10 mL) was added aqueous solution (5 mL) of 85% potassium hydroxide (0.20 g), and the mixture was stirred at room temperature for 18 hr. The reaction solution was concentrated under reduced pressure, and aqueous citric acid solution was added to the obtained residue. The mixture was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (205 mg, yield 93%) as pale-pink crystals. MS:341 (MH+).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, and aqueous citric acid solution
  2. additionwas added to the obtained residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0c86d2a0a35f4bd1830a72d5cae79493
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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