HCID 90404328, compound → HCID 90404362, compound

HRID 1772491Notes

Reaction equation

HRID 1772491 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[N:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]#[C:21][CH2:22][CH2:23][OH:24])=[CH:16][CH:15]=3)=[N:10]2)=[CH:5][CH:4]=1>[Pd].C(OCC)(=O)C>[F:26][C:2]([F:1])([F:25])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[N:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH2:23][OH:24])=[CH:16][CH:15]=3)=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 90404328HCID 90404328, compound

Product 1

HCID 90404362HCID 90404362, compoundYield 104%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 4-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)but-3-yn-1-ol (C61) (0.376 g, 0.967 mmol) in a 100 mL round bottomed flask equipped with a stir bar and septa was added ethyl acetate (9.67 mL) followed by palladium on carbon (0.103 g, 0.0970 mmol). The reaction mixture was evacuated with vacuum and purged with hydrogen (balloon) (2×) and stirred at room temperature overnight. The reaction mixture was filtered through Celite®, washed with ethyl acetate and concentrated to provide the title compound as a white solid (0.363 g, 104%): 1H NMR (400 MHz, CDCl3) δ 8.65 (s, 1H), 8.15-8.08 (m, 2H), 7.94-7.88 (m, 2H), 7.80 (dd, J=8.2, 1.1 Hz, 2H), 7.34-7.28 (m, 2H), 3.74-3.66 (m, 2H), 3.66-3.60 (m, 1H), 2.72 (t, J=7.6 Hz, 2H), 1.81-1.71 (m, 2H), 1.69-1.60 (m, 2H); 19F NMR (376 MHz, CDCl3) δ −62.48; ESIMS m/z 362 ([M+H]+).

Workup

  1. customThe reaction mixture was evacuated with vacuum
  2. custompurged with hydrogen (balloon) (2×)
  3. filtrationThe reaction mixture was filtered through Celite®
  4. washwashed with ethyl acetate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bcdc067a77854324aeba8d89343f730d
Source dataset
uspto-grants-2016_02
Patent number
US09249133B2

Reaction notes

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