Tetrahydrofuran → 4-(6,7-Dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-(n-propyl)benzonitrile

HRID 1877933Notes

Reaction equation

HRID 1877933 reaction equation
[CH:1]1[N:5]=[CH:4][N:3]2[CH:6]([C:9]3[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=3/[CH:17]=[CH:18]/[CH3:19])[CH2:7][CH2:8][C:2]=12.C1COCC1>[Pd].CCO>[CH:1]1[N:5]=[CH:4][N:3]2[CH:6]([C:9]3[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=3[CH2:17][CH2:18][CH3:19])[CH2:7][CH2:8][C:2]=12

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 588271824-(6,7-Dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-((E)-propenyl)benzonitrile

Product 1

HCID 588270944-(6,7-Dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-(n-propyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 4-(6,7-Dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-((E)-propenyl)benzonitrile (0.150 g, 0.602 mmol), 20% (w/w) palladium on carbon (0.040 g), THF (15 mL), and EtOH (15 mL) is stirred under an atmosphere of hydrogen (1 atm) for 60 h. The suspension is the filtered and the filtrate concentrated. The residue is then purified by flash chromatography (Hexane/EtOAc, and then 10% MeOH/EtOAc) to give 4-(6,7-Dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-(n-propyl)benzonitrile as a white solid. MS (ESI) m/z 252.1 (M+H); 1H NMR (400 MHz, CDCl3) δ ppm 1.04 (t, J=7.3 Hz, 3 H), 1.63-1.77 (m, 2 H), 2.33-2.45 (m, 1 H), 2.62-2.80 (m, 2 H), 2.92 (app t, J=7.1 Hz, 2 H), 3.04-3.19 (m, 1 H), 5.58 (dd, J=7.8, 5.6 Hz, 1 H), 6.73 (d, J=8.1 Hz, 1 H), 6.81 (s, 1 H), 7.25 (s, 1 H), 7.41 (d, J=8.1 Hz, 1 H), 7.51 (s, 1 H).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated
  3. customThe residue is then purified by flash chromatography (Hexane/EtOAc

Sources & evidence

ORD record
ord-6dcbe196f1bd4b319ee215fb5a971f3a
Source dataset
uspto-grants-2012_11
Patent number
US08314097B2

Reaction notes

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