HCID 58934740, compound → HCID 58934951, compound

HRID 855120Notes

Reaction equation

HRID 855120 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[C:8][C:9]1[CH:10]=[C:11]([O:26][C:27]([F:30])([F:29])[F:28])[CH:12]=[C:13]2[C:18]=1[O:17][CH:16]([C:19]([F:22])([F:21])[F:20])[C:15]([C:23]([OH:25])=[O:24])=[CH:14]2>CC(O)=O.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][C:9]1[CH:10]=[C:11]([O:26][C:27]([F:30])([F:28])[F:29])[CH:12]=[C:13]2[C:18]=1[O:17][CH:16]([C:19]([F:22])([F:21])[F:20])[C:15]([C:23]([OH:25])=[O:24])=[CH:14]2

Participants

4

Reactant 1

HCID 58934740HCID 58934740, compound

Product 1

HCID 58934951HCID 58934951, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 8-(pyridin-2-ylethynyl)-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid prepared as in Example 621j, Step 2 (684 mg, 1.59 mmole) and 10% Pd/C (100 mg) in glacial HOAc (20 mL) was hydrogenated at 20 psi for 2.5 h. The catalyst was filtrated, the solvent was removed in vacuo and the remaining HOAc was removed by azeotroping with hexanes to give the crude product as a tan solid. The solid was triturated with acetonitrile to give 362 mg (53% yield) of the product as an off-white solid: ESHRMS m/z 434.0834 (M+H, C19H14F6NO4, Calc'd 434.0822); 1H NMR (dmso-d6/300 MHz) 13.43 (brs, 1H), 8.50 (d, 1H, J=4.8 Hz), 7.90 (s, 1H), 7.67 (t, 1H, J=7.7 Hz), 7.46 (s, 1H), 7.26-7.17 (m, 3H), 6.06 (q, 1H, J=7.3 Hz), 3.32-3.01 (m, 4H).

Workup

  1. filtrationThe catalyst was filtrated
  2. customthe solvent was removed in vacuo
  3. customthe remaining HOAc was removed
  4. customby azeotroping with hexanes
  5. customto give the crude product as a tan solid
  6. customThe solid was triturated with acetonitrile

Sources & evidence

ORD record
ord-f52de97cca3f4a678077bcb619ef0358
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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