Methanol → HCID 71060591, compound

HRID 1038443Notes

Reaction equation

HRID 1038443 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH:11]=[O:12])=[CH:5]2.CO.C1(C)C=CC(S([CH2:24][N+:25]#[C-:26])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CCCCCC>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[O:12][CH:26]=[N:25][CH:24]=1)=[CH:5]2

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 189681295-Fluoro-1H-indole-2-carbaldehyde

Product 1

HCID 71060591HCID 71060591, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a 100 mL round-bottom flask was added 5-fluoro-1H-indole-2-carbaldehyde 47 (0.627 g, 3.84 mmol), methanol (40 mL), p-toluene sulfonylmethyl isocyanide (0.826 g, 4.23 mmol), followed by potassium carbonate (0.68 g, 4.92 mmol). The reaction mixture was stirred at reflux for about 1.5 hour and followed by TLC. The solvent was then evaporated and saturated aq. NaHCO3 was added. The resultant suspension was extracted with CH2Cl2 (2×20 mL). Combined organic layers were washed with brine, dried (anhydrous Na2SO4), and concentrated to leave a yellow solid. Crude product was further purified by silica-column chromatographed (Biotage) using Acetone:Hexane as an eluent to yield 5-(5-fluoro-1H-indol-2-yl)oxazole 48 (0.202 g, 72% yield). MS (ES) m/z 203 (M+H+).

Workup

  1. temperatureat reflux for about 1.5 hour
  2. customThe solvent was then evaporated
  3. additionsaturated aq. NaHCO3 was added
  4. extractionThe resultant suspension was extracted with CH2Cl2 (2×20 mL)
  5. washCombined organic layers were washed with brine
  6. dry with materialdried (anhydrous Na2SO4)
  7. concentrationconcentrated
  8. customto leave a yellow solid
  9. customCrude product was further purified by silica-column
  10. customchromatographed (Biotage)

Sources & evidence

ORD record
ord-d747993b00214255a76f80af23eebdeb
Source dataset
uspto-grants-2013_10
Patent number
US08551992B2

Reaction notes

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