Acetic Acid → HCID 86599496, compound

HRID 855121Notes

Reaction equation

HRID 855121 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([O:20][C:21]([F:24])([F:23])[F:22])[CH:6]=[C:7]2[C:12]=1[O:11][CH:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]([OH:19])=[O:18])=[CH:8]2)#[N:2].[C:25]([OH:28])(=[O:27])[CH3:26]>[Pd]>[F:14][C:13]([F:16])([F:15])[C:10]([OH:27])=[O:11].[C:25]([C:26]1[CH:10]([C:13]([F:14])([F:16])[F:15])[O:11][C:12]2[C:3]([CH:1]=1)=[CH:4][C:5]([O:20][C:21]([F:22])([F:23])[F:24])=[CH:6][C:7]=2[CH2:8][CH2:9][NH:2][CH2:1][C:3]1[CH:4]=[C:5]([O:20][C:21]([F:24])([F:22])[F:23])[CH:6]=[C:7]2[C:12]=1[O:11][CH:10]([C:13]([F:14])([F:15])[F:16])[C:9]([C:17]([OH:19])=[O:18])=[CH:8]2)([OH:28])=[O:27]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 11210373HCID 11210373, compound

Product 1

HCID 86599496HCID 86599496, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 8-cyano-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid prepared as in Example 21p, Step 2 (445 mg, 1.26 mmole) and 10% Pd/C (100 mg) in glacial acetic acid (20 mL) was hydrogenated at 20 psi for 1 h and the pressure released. After standing overnight, the catalyst filtered and the solvent was removed in vacuo. Purification by reverse phase chromatography (acetonitrile:0.5% TFA-H2O) gave 140 mg (32% yield) of the product: ESHRMS m/z 698.0694 (M+H, C26H16Fl2NO8, Calc'd 698.0679); 1H NMR (dmso-d6/300 MHz) 13.6 (brs, 1H), 13.1 (brs, 1H), 9.39 (brs, 2H), 9.39 (brs, 2H), 7.95-7.93 (m, 2H), 7.72-7.70 (m, 2H), 7.63-7.59 (m, 2H), 6.00-5.91 (m, 2H), 4.29-4.17 (m, 4H).

Workup

  1. waitAfter standing overnight
  2. filtrationthe catalyst filtered
  3. customthe solvent was removed in vacuo
  4. customPurification by reverse phase chromatography (acetonitrile:0.5% TFA-H2O)

Sources & evidence

ORD record
ord-30cf0a7ee0d64f9a9ad6c05e9aee8ec8
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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