(3-Cyanopropyl)triphenylphosphonium bromide → 5-[6-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-quinolin-2-yl]-penta-4-ennitrile

HRID 348747

Reaction equation

HRID 348747 reaction equation
[Br-].[C:2]([CH2:4]CC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:3].C([N-]C(C)C)(C)C.[Li+].CCCCCCC.[O:41]=[C:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44](=[O:51])[N:43]1[CH2:52][C:53]1[CH:54]=[C:55]2[C:60](=[CH:61][CH:62]=1)[N:59]=[C:58]([CH2:63][CH2:64][C:65]#N)[CH:57]=[CH:56]2>C1COCC1>[O:51]=[C:44]1[C:45]2[C:50](=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:42](=[O:41])[N:43]1[CH2:52][C:53]1[CH:54]=[C:55]2[C:60](=[CH:61][CH:62]=1)[N:59]=[C:58]([CH:63]=[CH:64][CH2:65][CH2:4][C:2]#[N:3])[CH:57]=[CH:56]2

Participants

5

Reactant 3

HCID 3036619(3-Cyanopropyl)triphenylphosphonium bromideHCID 210844023-[6-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-quinolin-2-yl]-propionitrileHCID 86599834LDA heptane

Product 1

HCID 669418485-[6-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-quinolin-2-yl]-penta-4-ennitrileYield 75.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The compound (675.0 mg) obtained in Example 123-1 was suspended in anhydrous THF (30 ml) and cooled with ice. Then, the suspension was added with a 2 mol/l lithium diisopropylamide/heptane solution (0.825 ml), followed by stirring at room temperature for 1 hour. Then, the solution was gradually added with a solution prepared by suspending the compound (327.9 mg) obtained in Example 119-7 in anhydrous THF (20 ml), followed by stirring at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (268.0 mg) as a yellow solid.

Workup

  1. temperaturecooled with ice
  2. additionThen, the solution was gradually added with a solution
  3. customprepared
  4. stirringby stirring at room temperature for 3 hours
  5. customAfter completion of the reaction
  6. distillationthe solvent was distilled off
  7. customthe residue was then purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-3f35a7569eac49428d37808066d592bb
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Linked notes

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