Triphenylphosphine → HCID 178454879, compound

HRID 505416Notes

Reaction equation

HRID 505416 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11][Cl:12])[NH:8][C:5]2=[N:6][CH:7]=1.[C:13]1([P:19]([C:26]2C=C[CH:29]=[CH:28][CH:27]=2)[C:20]2C=C[CH:23]=[CH:22][CH:21]=2)C=C[CH:16]=[CH:15][CH:14]=1>CN(C)C=O.C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl-:12].[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11][P+:19]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:13][CH2:14][CH2:15][CH3:16])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 11776TriphenylphosphineHCID 178478446HCID 178478446, compound2×

Product 1

HCID 178454879HCID 178454879, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

4.0 g of 6-bromo-2-chloromethyl-3H-imidazo[4,5-b]pyridine (compound B4) are suspended in 16 ml of N,N-dimethylformamide and 54 ml of acetonitrile. 4.9 ml of triphenylphosphine and 0.599 g of tetrabutylammonium iodide are added sequentially at 40° C. and the mixture is heated to 90° C. for 20 h. The mixture is concentrated to dryness to give the 8.94 g of the crude title compound as an oil, which is used as obtained. MS: 412.3, 414.2 (M+). TLC: Rf=0.40-0.55 (dichloromethane/methanol 10:1).

Workup

  1. concentrationThe mixture is concentrated to dryness

Sources & evidence

ORD record
ord-81a68f49890f4b7093ddfb3f89156edd
Source dataset
uspto-grants-2010_08
Patent number
US07781453B2

Reaction notes

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