Trifluoroacetic acid → HCID 86633021, compound

HRID 1919850Notes

Reaction equation

HRID 1919850 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[CH3:16])[CH3:2].O.[Na+:19].[CH:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28]([O-:31])(=[O:30])=[O:29])=O.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl.[Cl-].[Na+].O>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[C:8]([CH2:20][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[S:28]([O-:31])(=[O:30])=[O:29])=[C:7]1[CH3:16])[CH3:2].[Na+:19]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 16211671Sodium 2-formylbenzene-1-sulfonate--water (1/1/1)HCID 44185546Ethyl 2-(5-fluoro-2-methyl-1H-indol-1-yl)acetate

Product 1

HCID 86633021HCID 86633021, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of [5-fluoro-2-methyl-1H-indol-1-yl]acetic acid ethyl ester (2.16 g, 9.19 mmol) at room temperature in dichloromethane (80 mL), was added 2-formylbenzenesulfonic acid sodium salt hydrate (2.01 g, 9.66 mmol) followed by triethylsilane (7.6 mL, 47.8 mmol). TFA (2.24 mL, 29.1 mmol) was then added dropwise over 30 min, and after the addition was complete, the mixture was stirred at room temperature for 72 h. Saturated aqueous NaHCO3 (100 mL) was then added to the solution plus saturated brine (10 mL) and the product extracted with ethyl acetate (200 ml). The organic layer was washed with saturated brine (100 mL), dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The resulting pink sticky solid was triturated with ethanol and hexanes to give sodium 2-((1-(2-ethoxy-2-oxoethyl)-5-fluoro-2-methyl-1H-indol-3-yl)methyl)benzene-sulfonate (2.33 g, 5.45 mmol, 59%).

Workup

  1. additionafter the addition
  2. extractionthe product extracted with ethyl acetate (200 ml)
  3. washThe organic layer was washed with saturated brine (100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe resulting pink sticky solid was triturated with ethanol and hexanes

Sources & evidence

ORD record
ord-ba20dc76fea54aea8155132bf179aee1
Source dataset
uspto-grants-2012_05
Patent number
US08168673B2

Reaction notes

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