Triphenylphosphine → HCID 178437478, compound

HRID 505414Notes

Reaction equation

[Cl:1][CH:2]([C:4]1[NH:12][C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[N:5]=1)[CH3:3].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O.C(#N)C>[Cl-:1].[N:5]1[C:6]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[NH:12][C:4]=1[CH:2]([P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH3:3]

Participants

Conditions

Temperature: 150 °C

Procedure

8.66 g of 2-(1-chloroethyl)-3H-imidazo[4,5-b]pyridine (compound B2) are suspended in 40 ml of N,N-dimethylformamide and 120 ml of acetonitrile. 12.6 g of triphenylphosphine are added and the mixture is heated to 150° C. for 17 h. The mixture is concentrated to dryness and the crude product purified by chromatography on silica gel (eluent: dichloromethane/methanol 20:1) to afford 4.16 g of the title compound as an oil. MS: 408.0 (M+). TLC: Rf=0.22-0.47 (dichloromethane/methanol 10:1).

Workup

concentrationThe mixture is concentrated to dryness
customthe crude product purified by chromatography on silica gel (eluent: dichloromethane/methanol 20:1)

Sources & evidence

ORD record: ord-ed66a08d040446b89bcf946a4b5e91fb
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781453B2

Reaction notes

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