Triethylamine → 3-(Phenylthio)-1H-pyrrolo[2,3-b]pyridine
Reaction equation
[C:1]1([S:7]([CH3:9])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][N:30]=2)C=[CH:24]1.C(N(CC)CC)C>C(Cl)Cl>[C:1]1([S:7][C:9]2[C:26]3[C:31](=[N:30][CH:29]=[CH:28][CH:27]=3)[NH:23][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
A solution of methyl phenyl sulfoxide (8.33 g, 59.4 mmol) in CH2Cl2 is chilled to −78° C. and treated dropwise with trifluoroacetic anhydride (4.1 mL, 5.3 mmol). After stirring for 30 min at −78° C., a solution of 7-azaindole (5.2 g, 44.0 mmol) in CH2Cl2 is added. After 30 min at −78° C., triethylamine (74 mL, 534 mmol) is added and the reaction is allowed to reach ambient temperature. After stirring for 3.5 days, the reaction is concentrated in vacuo, treated with saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic extracts are combined and concentrated in vacuo. The resultant residue is crystallized from methanol/H2O and recrystallized from CH2Cl2/hexane to afford the title compound as an off-white solid, 1.26 g, mp 188-189° C., characterized by mass spectral analyses and HNMR analyses.
Workup
- waitAfter 30 min at −78° C.
- customto reach ambient temperature
- stirringAfter stirring for 3.5 days
- concentrationthe reaction is concentrated in vacuo
- additiontreated with saturated aqueous NaHCO3
- extractionextracted with CH2Cl2
- concentrationconcentrated in vacuo
- customThe resultant residue is crystallized from methanol/H2O
- customrecrystallized from CH2Cl2/hexane
Sources & evidence
- ORD record
- ord-a27df85393ae48279c0877305635dcb3
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06825212B2
Reaction notes
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