HCID 57781097, compound → HCID 57781140, compound

HRID 1690718Notes

Reaction equation

HRID 1690718 reaction equation
[CH:1]([C:3]1[N:7]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[O:10][C:9]2([CH3:20])[CH3:19])[CH:6]=[N:5][CH:4]=1)=[CH2:2]>CO.[Pd]>[CH2:1]([C:3]1[N:7]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[O:10][C:9]2([CH3:19])[CH3:20])[CH:6]=[N:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 57781097HCID 57781097, compound

Product 1

HCID 57781140HCID 57781140, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(5-vinyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one (0.049 g, 0.173 mmol) (Example 3) in methanol (1 mL) is added Pd/C (10% wt, 0.009 g, 0.009 mmol) and the flask is flushed with hydrogen. The mixture is stirred under balloon pressure. After 3 h, another portion of catalyst (0.009 g) is added. After 7 h, the mixture is filtered and concentrated in vacuo to give 4-(5-ethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one as a white solid; MS (ESI) m/z 271.2 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 1.25 (s, 3 H), 1.43 (br. s., 3 H), 1.56 (s, 3 H), 2.87 (br. s, 2 H), 5.55 (br. s, 1 H), 6.83 (s, 1 H), 7.17 (br. s, 1 H), 7.45 (d, J=7.6 Hz, 1 H), 7.67 (td, J=7.6, 1.0 Hz, 1 H), 7.78 (td, J=7.6, 1.3 Hz, 1 H), 8.24 (dd, J=7.6, 1.0 Hz, 1 H).

Workup

  1. custom0.009 g, 0.009 mmol) and the flask is flushed with hydrogen
  2. additionanother portion of catalyst (0.009 g) is added
  3. waitAfter 7 h
  4. filtrationthe mixture is filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-414e5db2bf4c4410aee91d7eb7a4c6db
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

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