HCID 21879634, compound → HCID 21879617, compound

HRID 724215Notes

Reaction equation

HRID 724215 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]#[C:10][C:11]([C:13]1[N:14]=[CH:15][N:16]([C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=1)=[O:12]>C(OCC)(=O)C.O1CCCC1.[C].[Pd]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][C:11]([C:13]1[N:14]=[CH:15][N:16]([C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:17]=1)=[O:12]

Participants

5

Reactant 1

HCID 21879634HCID 21879634, compound

Product 1

HCID 21879617HCID 21879617, compoundYield 95.5%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(Tetrahydro-2H-pyran-2-yloxy)-1-(1-trityl-1H-imidazol-4-yl)-2-butyn-1-one (29.63 g) was dissolved in a mixture of ethyl acetate (200 ml) and tetrahydrofuran (800 ml). 10% Palladium carbon (2.6 g) was added and the mixture was stirred at room temperature for 3 h under a hydrogen atmosphere. 10% Palladium carbon was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; ethyl acetate) to give the title compound (28.53 g) as a brown solid.

Workup

  1. custom10% Palladium carbon was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent; ethyl acetate)

Sources & evidence

ORD record
ord-6cc1626a2e544c85aa877df8b295563e
Source dataset
uspto-grants-2006_11
Patent number
US07141598B2

Reaction notes

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