HCID 57781108, compound → HCID 57781121, compound

HRID 1690722Notes

Reaction equation

HRID 1690722 reaction equation
[C:1]([C:4]1[N:8]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[O:11][C:10]2([CH3:21])[CH3:20])[CH:7]=[N:6][CH:5]=1)([CH3:3])=[CH2:2]>CO.[Pd]>[CH:1]([C:4]1[N:8]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[O:11][C:10]2([CH3:21])[CH3:20])[CH:7]=[N:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 57781108HCID 57781108, compound

Product 1

HCID 57781121HCID 57781121, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(5-isopropenyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one (0.225 g, 0.797 mmol) (Example 4) in methanol (5 mL) is added Pd/C (0.250 g). The reaction vessel is flushed with hydrogen gas and stirred under balloon pressure for 72 h. The mixture is filtered and the filtrate concentrated in vacuo to give a 4-(5-isopropyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one(0.210 g) as yellow solid (ESI) m/z 285.0 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 1.24 (s, 3 H), 1.41 (d, J=6.6 Hz, 3 H), 1.45 (d, J=6.8 Hz, 3 H), 1.56 (s, 3H), 3.23 (br. s, 1 H), 5.60 (br. s, 1 H), 6.88 (br. s, 1 H), 7.15 (br. s, 1 H), 7.44 (d, J=7.3 Hz, 1H), 7.68 (td, J=7.6, 1.1 Hz, 1 H), 7.79 (td, J=7.6, 1.3 Hz, 1 H), 8.25 (dd, J=7.8, 1.3 Hz, 1 H).

Workup

  1. customThe reaction vessel is flushed with hydrogen gas
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-d4e77911eb5e4f699fc0a9a0412ec9f9
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

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