Triphenylphosphine → HCID 86632294, compound

HRID 885438Notes

Reaction equation

HRID 885438 reaction equation
O[CH2:2][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]=3[CH2:10][CH2:11][C:5]=2[CH:4]=1.[Cl:21][C:22]1[N:27]=[C:26]2[NH:28][C:29]([CH2:31][CH3:32])=[N:30][C:25]2=[C:24]([CH3:33])[CH:23]=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>[Cl:21][C:22]1[N:27]=[C:26]2[N:28]([CH2:2][C:3]3[CH:20]=[CH:19][C:6]4/[C:7](=[CH:16]/[C:17]#[N:18])/[C:8]5[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=5[CH2:10][CH2:11][C:5]=4[CH:4]=3)[C:29]([CH2:31][CH3:32])=[N:30][C:25]2=[C:24]([CH3:33])[CH:23]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 67211053HCID 67211053, compoundHCID 178437420HCID 178437420, compound

Product 1

HCID 86632294HCID 86632294, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[step 1] (E)-(2-Hydroxymethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile (120 mg, 0.46 mmol) and 5-chloro-2-ethyl-7-methyl-3H-imidazo[4,5-b]pyridine (117 mg, 0.60 mmol) were dissolved in THF (6.6 mL) and the solution was added with polymer supported triphenylphosphine (469 mg, 0.92 mmol) and di-t-butyl azodicarboxylate (211 mg, 0.92 mmol) at 0° C., followed by stirring at room temperature for 2 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=3/1) to give (E)-[2-(5-chloro-2-ethyl-7-methyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (90 mg, 45%).

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=3/1)

Sources & evidence

ORD record
ord-9a8b4d99ed6d4f3ca7da70a9f815e334
Source dataset
uspto-grants-2012_08
Patent number
US08242151B2

Reaction notes

Loading…