1,2-Dichloroethane → N-Methoxy-N-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamide
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[C:3]([C:10]([OH:12])=O)=[CH:2]1.C1C=NC2N(O)N=NC=2C=1.Cl.[CH3:24][NH:25][O:26][CH3:27].C(Cl)CCl.CCN(C(C)C)C(C)C.[Cl-].[NH4+]>O1CCOCC1>[CH3:27][O:26][N:25]([CH3:24])[C:10]([C:3]1[C:4]2[C:9](=[N:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)=[O:12]Participants
8
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 7-azaindole-3-carboxylic acid (324 mg, 2.00 mmol) in dioxane (10 mL) was added HOAt (300 mg, 2.20 mmol), N,O-Dimethylhydroxylamine hydrochloride (214 mg, 2.00 mmol) and EDC (422 mg, 2.20 mmol). The mixture was stirred at rt for 15 minutes then DIPEA (853 mg, 6.60 mmol) added slowly over 5 minutes. The reaction was then stirred at rt for an additional 18 hrs. The reaction was then poured into 25% ammonium chloride solution (10 mL) and extracted with EtOAc (3×10 mL). The combined extracts were dried over magnesium sulfate, filtered and concentrated to a brown oil. This oil was purified via column chromatography (SiO2, EtOAc) to afford the title compound as a viscous clear oil which solidified on standing. Yield=86%
Workup
- stirringThe reaction was then stirred at rt for an additional 18 hrs
- extractionextracted with EtOAc (3×10 mL)
- dry with materialThe combined extracts were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated to a brown oil
- customThis oil was purified via column chromatography (SiO2, EtOAc)
Sources & evidence
- ORD record
- ord-6687b67329e24560bb057cc8e5c8ce3e
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697697B2
Reaction notes
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