Sodium Iodide → HCID 86586104, compound

HRID 1861020Notes

Reaction equation

HRID 1861020 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[C:12]([C:18]#[C:19][C:20]([C:22]3[N:23](C(OC(C)(C)C)=O)[CH:24]=[C:25]([CH3:28])[C:26]=3[CH3:27])=[O:21])[C:13]([F:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[O:36]C(OC(C)(C)C)=O)=O)(C)(C)C.[I-:44].[Na+].C(O)(C(F)(F)F)=O>C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[F:17][C:13]1[C:12]([C:18]([I:44])=[CH:19][C:20](=[O:21])[C:22]2[NH:23][CH:24]=[C:25]([CH3:28])[C:26]=2[CH3:27])=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:8][C:9](=[O:36])[CH2:10]2

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 6422Trifluoroacetic acidHCID 10282105HCID 10282105, compound

Product 1

HCID 86586104HCID 86586104, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of 2-tert-butoxycarbonyloxy-4-[3-(1-tert-butoxycarbonyl-3,4-dimethyl-1H-pyrrol-2-yl)-3-oxo-prop-1-ynyl]-5-fluoro-indole-1-carboxylic acid tert-butyl ester (from Example 47 above) (0.79 g, 1.33 mmol) and sodium iodide (Aldrich, 0.50 g, 3.33 mmol) was slowly added TFA (Aldrich, 15 mL) at room temperature. The reaction mixture was stirred at room temperature for 1.5 hours, and then diluted with ethyl acetate and saturated aqueous sodium bicarbonate solution. After separation, the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was triturated with ethyl acetate, filtered, and dried to give 5-fluoro-4-[1-iodo-3-oxo-3-(3,4-dimethyl-1H-pyrrol-2-yl)-propenyl]-1,3-dihydro-indol-2-one as a brown solid which was used in the next step without further purification. (Yield 0.40 g, 71.4%).

Workup

  1. customat room temperature
  2. customAfter separation
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was triturated with ethyl acetate
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-9659330c21104cdca0399b1a7f6a9fae
Source dataset
uspto-grants-2003_03
Patent number
US06531598B1

Reaction notes

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