Triphenylphosphine → HCID 69020207, compound

HRID 885442Notes

Reaction equation

HRID 885442 reaction equation
OC[C:3]1[CH:20]=[CH:19][C:6]2/[C:7](=[CH:16]/[C:17]#[N:18])/[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3CC[C:5]=2[CH:4]=1.[CH2:21]([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)[CH3:22].[C:34]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=N[C:55](OC(C)(C)C)=[O:56]>C1COCC1>[CH2:21]([C:23]1[N:33]([CH2:34][C:3]2[CH:20]=[CH:19][C:6]3=[C:5]([CH:4]=2)[O:56][CH2:55][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2/[C:7]/3=[CH:16]\[C:17]#[N:18])[C:26]2=[N:27][C:28]([CH3:32])=[CH:29][C:30]([CH3:31])=[C:25]2[N:24]=1)[CH3:22]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 67211053HCID 67211053, compoundHCID 178437439HCID 178437439, compound

Product 1

HCID 69020207HCID 69020207, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[step 1] (E)-(3-Hydroxymethyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)acetonitrile (JP-B-2526005; 250 mg, 0.950 mmol) and 2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine (250 mg, 1.42 mmol) were dissolved in THF (9.5 mL), and the solution was added with polymer supported triphenylphosphine (633 mg, 1.90 mmol) and di-t-butyl azodicarboxylate (437 mg, 1.90 mmol) at 0° C., followed by stirring at room temperature for 3 hr. The mixture was filtrated and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give (E)-[3-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]acetonitrile (158 mg, 26%).

Workup

  1. additionthe solution was added with polymer
  2. customat 0° C.
  3. filtrationThe mixture was filtrated
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-3b81285a72c4481a986e50446f16d966
Source dataset
uspto-grants-2012_08
Patent number
US08242151B2

Reaction notes

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