Triphenylphosphine → HCID 69952084, compound

HRID 1699534Notes

Reaction equation

HRID 1699534 reaction equation
C(O[C@@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([C:20]3[N:24]([C:25]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]([CH3:34])[CH:26]=4)[C:23](=[O:35])[N:22]([CH2:36][C:37]4[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][C:38]=4[O:45][CH3:46])[C:21]=3[C:47]#[N:48])=[CH:12]2)[CH:7]=[CH:6]1)(=O)C.[C:49]1(=O)[NH:53][C:52](=O)[C:51]2=[CH:55][CH:56]=[CH:57][CH:58]=[C:50]12.[K].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Li+]>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].CN(C=O)C>[C:47]([C:21]1[N:22]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][C:38]=2[O:45][CH3:46])[C:23](=[O:35])[N:24]([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH3:34])[CH:26]=2)[C:20]=1[C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]([C@H:8]2[CH2:9][CH2:10][C@@H:5]([N:53]3[CH2:49][C:50]4[C:51](=[CH:55][CH:56]=[CH:57][CH:58]=4)[CH2:52]3)[CH:6]=[CH:7]2)[CH:12]=1)#[N:48]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 24194345Phthalimide potassium saltHCID 69952465HCID 69952465, compound

Product 1

HCID 69952084HCID 69952084, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

In a flask was added 0.064 g (0.10 mmole) of the product obtained in step b), 0.046 g (0.25 mmole) of potassium phthalimide, 0.0096 g (0.01 mmole) of Pd2(dba)3, 0.013 g (0.05 mmole) of triphenylphosphine, 1 mg of lithium chloride and finally 7 ml of dry DMF. The flask was sealed and stirred under nitrogen at 70° C. under nitrogen for 90 minutes. The mixture was partitioned between EtOAc and water, and the organic phase was collected and concentrated. The residue was purified on silica (Heptane:EtOAc 1:3), giving 0.040 g (55%) of the sub-title compound as a white solid.

Workup

  1. customThe flask was sealed
  2. customThe mixture was partitioned between EtOAc and water
  3. customthe organic phase was collected
  4. concentrationconcentrated
  5. customThe residue was purified on silica (Heptane:EtOAc 1:3)

Sources & evidence

ORD record
ord-4b3be7156d544783beb57e472f1c16bb
Source dataset
uspto-grants-2002_02
Patent number
US06346625B1

Reaction notes

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