Triphenylphosphine → HCID 12001588, compound

HRID 503217Notes

Reaction equation

HRID 503217 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][O:7][CH2:8][C:9]1[CH:10]=[C:11]([N:15]2[C:19]3[CH:20]=[CH:21][C:22]([CH2:24]O)=[CH:23][C:18]=3[N:17]=[CH:16]2)[CH:12]=[CH:13][CH:14]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P([N:73]=[N+:74]=[N-:75])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[N:73]([CH2:24][C:22]1[CH:21]=[CH:20][C:19]2[N:15]([C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([CH2:8][O:7][CH2:6][C:2]4[S:1][CH:5]=[CH:4][N:3]=4)[CH:10]=3)[CH:16]=[N:17][C:18]=2[CH:23]=1)=[N+:74]=[N-:75]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 5363146Diisopropyl azodicarboxylateHCID 12001584HCID 12001584, compound

Product 1

HCID 12001588HCID 12001588, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 10g (0.1 g; 0.28 mmol) and PPh3 (0.11 g; 0.43 mmol) in THF (3 ml) was added DIAD (0.09 g; 0.43 mmol) at 0° C. After 5 min. diphenylphosphorylazide (0.12 g; 0.43 mmol) was added and the mixture was allowed to reach room temperature. Stirring was continued for 2 hours. The solvent was removed by evaporation and the residue was eluted through silica gel with a mixture of dichloromethane and methanol (50:1 v/v) to afford 25g. LC-ESI-HRMS of [M+H]+ shows 377.1188 Da. Calc. 377.118455 Da, dev. 0.9 ppm In analogy herewith the following compounds were prepared 5-Azidomethyl-1-[3-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxymethyl)-phenyl]-1H-benzoimidazole (25c) from 10c. LC-ESI-HRMS of [M+H]+ shows 375.1671 Da. Calc. 375.168182 Da, dev. −2.9 ppm 5-Azidomethyl-1-[3-(2-methyl-2H-pyrazol-3-ylmethoxymethyl)-phenyl]-1H-benzoimidazole (25e) from 10e. LC-ESI-HRMS of [M+H]+ shows 374.1732 Da. Calc. 374.172925 Da, dev. 0.7 ppm

Workup

  1. customto reach room temperature
  2. customThe solvent was removed by evaporation
  3. washthe residue was eluted through silica gel with a mixture of dichloromethane and methanol (50:1 v/v)

Sources & evidence

ORD record
ord-2b10398a81624e178606a048fac5691d
Source dataset
uspto-grants-2010_08
Patent number
US07776900B2

Reaction notes

Loading…