Triphenylphosphine → (Z)-2-[3-(2,5,7-trimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]propiononitrile

HRID 452153Notes

Reaction equation

HRID 452153 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2=[C:7]([CH:21]=1)[O:8][CH2:9][C:10]1[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=1/[C:12]/2=[C:13](\[CH3:16])/[C:14]#[N:15].[CH3:22][C:23]1[NH:33][C:26]2=[N:27][C:28]([CH3:32])=[CH:29][C:30]([CH3:31])=[C:25]2[N:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH3:22][C:23]1[N:33]([CH2:2][C:3]2[CH:4]=[CH:5][C:6]3=[C:7]([CH:21]=2)[O:8][CH2:9][C:10]2[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=2/[C:12]/3=[C:13](\[CH3:16])/[C:14]#[N:15])[C:26]2=[N:27][C:28]([CH3:32])=[CH:29][C:30]([CH3:31])=[C:25]2[N:24]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 67210707(Z)-2-(3-Hydroxymethyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)propiononitrileHCID 178423971HCID 178423971, compound

Product 1

HCID 67210475(Z)-2-[3-(2,5,7-trimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]propiononitrileYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[step 1] (Z)-2-(3-Hydroxymethyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)propiononitrile (400 mg, 1.44 mmol) obtained in Reference Example B6 and 2,5,7-trimethyl-3H-imidazo[4,5-b]pyridine (U.S. Pat. No. 5,332,744; 349 mg, 2.16 mmol) were dissolved in THF (14 mL), polymer-supported triphenylphosphine (962 mg, 2.88 mmol) and di-tert-butyl azodicarboxylate (664 mg, 2.88 mmol) were added at 0° C., and the mixture was stirred at room temperature for 2 hr. The mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/6) to give (Z)-2-[3-(2,5,7-trimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]propiononitrile (310 mg, 51%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/6)

Sources & evidence

ORD record
ord-fb15ce1d9dd74696903b3eb1f725dafc
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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