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Triphenylphosphine → 2-(4-{2-[4-(3,5-Dimethyl-pyridin-4-yl)-3,5-dimethyl-phenyl]-vinyl}-phenyl)-malononitrile

HRID 1169537
Notes
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Reaction equation

HRID 1169537 reaction equation
I[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:14]([CH3:15])=[CH:13][N:12]=[CH:11][C:10]=2[CH3:16])=[C:4]([CH3:17])[CH:3]=1.[CH:18]([C:20]1[CH:25]=[CH:24][C:23]([CH:26]([C:29]#[N:30])[C:27]#[N:28])=[CH:22][CH:21]=1)=[CH2:19].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:16][C:10]1[CH:11]=[N:12][CH:13]=[C:14]([CH3:15])[C:9]=1[C:5]1[C:6]([CH3:8])=[CH:7][C:2]([CH:19]=[CH:18][C:20]2[CH:25]=[CH:24][C:23]([CH:26]([C:27]#[N:28])[C:29]#[N:30])=[CH:22][CH:21]=2)=[CH:3][C:4]=1[CH3:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 58510520HCID 58510520, compoundHCID 585105282-(4-Vinyl-phenyl)-malononitrile

Product 1

HCID 723235872-(4-{2-[4-(3,5-Dimethyl-pyridin-4-yl)-3,5-dimethyl-phenyl]-vinyl}-phenyl)-malononitrileYield 55.4%

Reagents, catalysts & solvents 1

HCID 167845
palladium(II) acetate
Catalyst

Conditions

Temperature
100 °C

Procedure

A flame-dried sealable Schlenk tube was charged with 11 (3.37 g, 10.0 mmol), 18 (2.52 g, 15.0 mmol), Pd(OAc)2 (224 mg, 1.00 mmol), and PPh3 (262 mg, 1.00 mmol), evacuated, and then backfilled with N2. Next, dry Et3N (5 mL) and dry DMF (10 mL) were added under an N2 flow. The Schlenk tube was sealed, and the mixture was degassed by 3 freeze-thaw cycles and backfilled with N2. The mixture was then covered with aluminum foil and stirred at 100° C. for 2 days. The reaction mixture was next cooled to room temperature, poured into water, neutralized with dilute HCl to pH=7, and extracted with CH2Cl2 (3×50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was then purified by flash chromatography on silica gel, eluting with 1:1 hexane: ethyl acetate to give 2.09 g (55.4%) of the title compound as red solid: mp 58-60° C.; 1H NMR (400 MHz, CDCl3): δ 8.405 (s, 2H), 7.640 (d, 2H, J=8.0 Hz), 7.506 (d, 2H, J=8.0 Hz), 7.337 (s, 2H), 7.160 (s, 2H), 1.936 (s, 6H), 1.929 (s, 6H); 13C NMR (100 MHz, CDCl3): δ 148.657, 148.093, 139.804, 137.383, 135.973, 135.218, 130.978, 127.911, 127.757, 126.774, 126.410, 124.863, 111.915, 28.096, 19.988, 16.749; MS (ESI): m/z 378.5 [M++H,100];MS (high resolution, EI): m/z 377.1878 [M+]; calcd, 377.1892; Anal. Calcd. for C26H23N3·1/2 H2O: C, 80.80; H, 6.26; N, 10.87. Found; C, 80.22; H, 6.32; N, 10.28.

Workup

  1. customevacuated
  2. additionNext, dry Et3N (5 mL) and dry DMF (10 mL) were added under an N2 flow
  3. customThe Schlenk tube was sealed
  4. customthe mixture was degassed by 3 freeze-thaw cycles
  5. temperatureThe reaction mixture was next cooled to room temperature
  6. additionpoured into water
  7. extractionextracted with CH2Cl2 (3×50 mL)
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude product was then purified by flash chromatography on silica gel
  12. washeluting with 1:1 hexane

Sources & evidence

ORD record
ord-9dcaaf2cea4a492b946584ae1f0223de
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07824582B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes