Triphenylphosphine → 2-(1-Azidoethyl)-3-phenyl-1-(toluene-4-sulfonyl)-1H-indole
Reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:34]1([C:40]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[N:42]([S:49]([C:52]3[CH:57]=[CH:56][C:55]([CH3:58])=[CH:54][CH:53]=3)(=[O:51])=[O:50])[C:41]=2[CH:59](O)[CH3:60])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C1(P([N:76]=[N+:77]=[N-:78])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCOCC1.C(Cl)Cl>[N:76]([CH:59]([C:41]1[N:42]([S:49]([C:52]2[CH:57]=[CH:56][C:55]([CH3:58])=[CH:54][CH:53]=2)(=[O:50])=[O:51])[C:43]2[C:48]([C:40]=1[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH3:60])=[N+:77]=[N-:78]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of DIAD (1.80 g, 8.89 mmol) in dioxane (5 mL) was added to a solution of triphenylphosphine (2.33 g, 8.89 mmol) in dioxane (20 mL) at 0° C. under a nitrogen atmosphere. After 10 min stirring, 1-[3-phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]ethanol (1.74 g, 4.44 mmol) in dioxane (15 mL) was added followed by diphenylphosphoryl azide (1.47 g, 5.53 mmol) in dioxane (5 mL). The reaction mixture was stirred at 20° C. for 16 h then the reaction mixture was diluted with DCM and purified by column chromatography (Si—PCC, gradient 10-100% DCM in pentane) affording the title compound as a gum (1.39 g, 75%). LCMS (Method C): RT 4.77 min [M-N3]+ 374.1.
Workup
- stirringThe reaction mixture was stirred at 20° C. for 16 h
- custompurified by column chromatography (Si—PCC, gradient 10-100% DCM in pentane)
Sources & evidence
- ORD record
- ord-8a38f60995c7463282ff66570af9ef7a
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653089B2
Reaction notes
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