HCID 58934539, compound → HCID 52941415, compound

HRID 854912Notes

Reaction equation

HRID 854912 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([O:21][C:22]([F:25])([F:24])[F:23])[CH:7]=[C:8]2[C:13]=1[O:12][CH:11]([C:14]([F:17])([F:16])[F:15])[C:10]([C:18]([OH:20])=[O:19])=[CH:9]2)#[C:2][CH3:3]>[Pd].CCO>[CH2:1]([C:4]1[CH:5]=[C:6]([O:21][C:22]([F:25])([F:23])[F:24])[CH:7]=[C:8]2[C:13]=1[O:12][CH:11]([C:14]([F:17])([F:16])[F:15])[C:10]([C:18]([OH:20])=[O:19])=[CH:9]2)[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 58934539HCID 58934539, compound

Product 1

HCID 52941415HCID 52941415, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a Paar bottle was added 8-prop-1-ynyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid prepared as in Example 21 d, Step 2 (150 mg, 0.409 mmole), 10% Pd/C (75 mg) and absolute EtOH (10 mL). The mixture was hydrogenated at 30 psi for 2 h. The catalyst was filtered, the solvent was removed in vacuo and the resulting oily solid triturated with hexanes to give 76 mg (50% yield) of the product as an off-white solid: ESHRMS m/z 369.0559 (M−H, C15H11F6O4, Calc'd 369.0556). 1H NMR (dmso-d6, 300 MHz) 13.38 (brs, 1H), 7.87 (s, 1H), 7.43 (s, 1H), 7.26 (s, 1H), 5.99 (q, 1H, J=7.3 Hz), 2.51-2.66 (m, 2H), 1.48-1.60 (m, 2H), 0.86 (t, 3H, J=7.3 Hz).

Workup

  1. additionTo a Paar bottle was added
  2. filtrationThe catalyst was filtered
  3. customthe solvent was removed in vacuo
  4. customthe resulting oily solid triturated with hexanes

Sources & evidence

ORD record
ord-024b6add140d49a295d4718f26a3c5a8
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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