HCID 69018939, compound → HCID 69018966, compound

HRID 1865113Notes

Reaction equation

HRID 1865113 reaction equation
[C:1]([C:3]1[C:4]([C:18]2[CH:23]=[CH:22][C:21]([O:24]CC3C=CC=CC=3)=[CH:20][CH:19]=2)=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]([CH3:12])[C:7]=1[C:8]([F:11])([F:10])[F:9])#[N:2].[H][H]>[OH-].[OH-].[Pd+2].C(O)C.C1COCC1>[C:1]([C:3]1[C:4]([C:18]2[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=2)=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]([CH3:12])[C:7]=1[C:8]([F:11])([F:9])[F:10])#[N:2]

Participants

5

Reactant 2

HCID 69018939HCID 69018939, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69018966HCID 69018966, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

In a manner analogous to the procedure set forth in Scheme II, step A, hydrogenate ethyl 4-cyano-1-methyl-3-[4-(phenylmethoxy)phenyl]-5-(trifluoromethyl)pyrrole-2-carboxylate, (intermediate prepared in example A-237) using Pearlman's catalyst and 60 psi of hydrogen gas in 1:1 ethanol/THF for 11 hours. Filter the reaction through diatomaceous earth and concentrate in vacuo. Purify the residue via radial chromatography eluting with ethyl acetate and hexane to provide the title compound. MS (m/e): 337.0 (M−1) 1H NMR: 7.20 (d, 2H, J=8.3 Hz), 6.84 (d, 2H, J=8.8 Hz), 5.85 (s, 1H), 4.16 (q, 2H, J=7.0 Hz), 4.05 (s, 3H), 1.07 (t, 3H, J=7.0 Hz)

Workup

  1. customfor 11 hours
  2. filtrationFilter
  3. customthe reaction through diatomaceous earth
  4. concentrationconcentrate in vacuo
  5. customPurify the residue via radial chromatography
  6. washeluting with ethyl acetate and hexane

Sources & evidence

ORD record
ord-351827c889d54699b5e9cbd1f7253837
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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