3-(4-(4-Phenylthiazol-2-yl)but-3-yn-1-yl)benzonitrile → 3-(4-(4-Phenylthiazol-2-yl)butyl)benzonitrile

HRID 1397368Notes

Reaction equation

HRID 1397368 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:12]#[C:13][CH2:14][CH2:15][C:16]3[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=3)[C:19]#[N:20])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].C(O)C>[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=3)[C:19]#[N:20])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 673238153-(4-(4-Phenylthiazol-2-yl)but-3-yn-1-yl)benzonitrile

Product 1

HCID 673250353-(4-(4-Phenylthiazol-2-yl)butyl)benzonitrileYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on charcoal (215 mg) was added to a solution of 3-(4-(4-phenylthiazol-2-yl)but-3-yn-1-yl)benzonitrile (430 mg, 1.37 mmol) in ethanol (15 mL), the reaction mixture was put under ˜2 kg H2-pressure for 48 h. The reaction mixture was filtered through a celite bed and washed thoroughly with EtOAc. The solvent was concentrated under reduced pressure to obtain 3-(4-(4-phenylthiazol-2-yl)butyl)benzonitrile (330 mg, 76%) as colorless viscous liquid. 1H NMR (300 MHz, CDCl3) δ 7.90-7.87 (m, 2H), 7.50-7.33 (m, 8H), 3.13-3.08 (t, J=7.5 Hz, 2H), 2.75-2.70 (t, J=7.5 Hz, 2H), 1.93-1.85 (m, 2H), 1.83-1.75 (m, 2H). MS (ESI) m/z: Calculated for C20H18N2S: 318.12. found: 319.2 (M+H)+.

Workup

  1. customfor 48 h
  2. filtrationThe reaction mixture was filtered through a celite bed
  3. washwashed thoroughly with EtOAc
  4. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-29ee646ebc644b31b426ee1bc7eb2df1
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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