Triphenylphosphine → HCID 69951119, compound

HRID 1699533Notes

Reaction equation

HRID 1699533 reaction equation
[C:1]([C:3]1[N:4]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=2[O:37][CH3:38])[C:5](=[O:27])[N:6]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH3:26])[CH:18]=2)[C:7]=1[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)#[N:2].[H-].[Li+].C(O[C@H:45]1[CH2:50][CH2:49][C@@H:48]([O:51][Si:52]([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:54])[CH3:53])[CH:47]=[CH:46]1)(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cl-].[Li+]>[Si:52]([O:51][C@@H:48]1[CH2:49][CH2:50][C@H:45]([N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]([C:7]3[N:6]([C:17]4[C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]([CH3:26])[CH:18]=4)[C:5](=[O:27])[N:4]([CH2:28][C:29]4[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=4[O:37][CH3:38])[C:3]=3[C:1]#[N:2])=[CH:9]2)[CH:46]=[CH:47]1)([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:54])[CH3:53]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 62714Lithium hydrideHCID 10978542HCID 10978542, compoundHCID 183207294-Cyano-3-(2,4-dimethoxybenzyl)-5-(3-indolyl)-1-(1-methyl-3-indolyl)-2,3-dihydroimidazol-2-one

Product 1

HCID 69951119HCID 69951119, compoundYield 85.5%

Reagents, catalysts & solvents 3

HCID 433294Lithium ChlorideCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

In a flask was added 0.30 g (0.59 mmole) of the product obtained in Example 17 step b), 0.012 g (1.5 mmole) of lithium hydride and 5 ml of dry DMF. The mixture was stirred under nitrogen at 60° C. for 45 min. The solution was degassed, and a solution of 0.16 g (0.59 mmole) of (1S,4R)-1-Acetoxy-4-(tert-butyldimethylsilanyloxy)-2-cyclohexene, 0.030 g (0.033 mmole) of Pd2(dba)3, 0.046 g (0.17 mmole) of triphenylphosphine, 2 mg of lithium chloride in 5 ml of DMF was added rapidly. The resulting solution was degassed again and stirred at 70° C. for 90 minutes. The solution was partitioned between ethyl acetate and water. The organic phase was collected and concentrated. The residue was purified on silica (Heptane:EtOAc 3:2) giving 0.36 g (85%) of the subtitle compound.

Workup

  1. customThe solution was degassed
  2. customThe resulting solution was degassed again
  3. stirringstirred at 70° C. for 90 minutes
  4. customThe solution was partitioned between ethyl acetate and water
  5. customThe organic phase was collected
  6. concentrationconcentrated
  7. customThe residue was purified on silica (Heptane:EtOAc 3:2)

Sources & evidence

ORD record
ord-3fe55f05b8fb4620a9be2675cd60b07d
Source dataset
uspto-grants-2002_02
Patent number
US06346625B1

Reaction notes

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