Triphenylphosphine → HCID 178478234, compound

HRID 2250380Notes

Reaction equation

HRID 2250380 reaction equation
[Cl:1][CH2:2][C:3]1[NH:11][C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=1.[C:12]1([P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C=O.C(#N)C>[Cl-:1].[N:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[NH:11][C:3]=1[CH2:2][P+:18]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 178478448HCID 178478448, compound

Product 1

HCID 178478234HCID 178478234, compoundYield 38.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

3.18 g of chloromethyl-3H-imidazo[4,5-b]pyridine (G. Cleve et al., Liebigs Ann. Chem. 1971, 747, 158-171) are suspended in 16 ml of N,N-dimethylformamide and 50 ml of acetonitrile. 4.98 g of triphenylphosphine are added and the mixture is heated to 100° C. for 3 h. The mixture is concentrated to dryness and the crude product purified by chromatography on silica gel (eluent: dichloromethane/methanol 10:1 to 8:1) to afford 3.15 g of the title compound as a beige, amorphous solid. M.p. 302° C. MS: 394.3 (M+). TLC: Rf=0.17-0.50 (dichloromethane/methanol 10:1).

Workup

  1. concentrationThe mixture is concentrated to dryness
  2. customthe crude product purified by chromatography on silica gel (eluent: dichloromethane/methanol 10:1 to 8:1)

Sources & evidence

ORD record
ord-af6e158f24ca47d782d4b57f7f67f650
Source dataset
uspto-grants-2008_01
Patent number
US07317021B2

Reaction notes

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