Trifluoroacetic acid → HCID 68380251, compound

HRID 2178665Notes

Reaction equation

HRID 2178665 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[NH:10][C:11](N)=[S:12].C[Si](OP(=O)=O)(C)C.C(=O)(O)[O-].[Na+].[F:27][C:28]([F:33])([F:32])C(O)=O>>[F:1][C:2]1[C:3]2[N:10]=[C:11]([C:28]([F:33])([F:32])[F:27])[S:12][C:4]=2[C:5]([OH:8])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 16133246Trimethyl(phosphooxy)silaneHCID 80212359HCID 80212359, compound

Product 1

HCID 68380251HCID 68380251, compound

Conditions

Temperature
95 °C

Procedure

A mixture containing crude 3-amino-4-fluoro-2-sulfanylphenol (C15) (Step 1) and polyphosphoric acid trimethylsilyl ester (10 mL) in trifluoroacetic acid (20 mL) was stirred at 95° C. for 18 hours. After cooling to room temperature the reaction was treated with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane (3×10 mL). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 30% tert-butyl methyl ether in heptanes) afforded the title compound as a solid. Yield: 1.66 g, 7.0 mmol, 59%. GCMS m/z 237 (M+). 1H NMR (400 MHz, CD3OD) δ 6.90 (dd, J=8.7, 3.3 Hz, 1H), 7.21 (dd, J=10.2, 8.7 Hz, 1H).

Workup

  1. temperatureAfter cooling to room temperature the reaction
  2. extractionextracted with dichloromethane (3×10 mL)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification via silica gel chromatography (Gradient: 0% to 30% tert-butyl methyl ether in heptanes)

Sources & evidence

ORD record
ord-0477e6aeeab34f5c969c1a77c583a0c7
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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