Triethylamine → N-methoxy-N-methyl-1H-indole-2-carboxamide
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.F[P-](F)(F)(F)(F)F.[N:20]1([O:29][C:30](N(C)C)=[N+](C)C)[C:24]2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.CNOC>CN(C)C=O>[CH3:30][O:29][N:20]([CH3:24])[C:10]([C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:12]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1H-indole-2-carboxylic acid (from Aldrich, 2.5 g, 16 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (7.6 g, 20 mmol) and triethylamine (11 mL, 78 mmol) in N,N-dimethylformamide (20 mL) was stirred at room temperature for 10 minutes. N,O-Dimethylhydroxylamine hydrochloride (2.0 g, 20 mmol) was added and the resulting suspension was stirred at room temperature for 2 hours. The mixture was quenched with water, extracted with EtOAc. The combined organic layers were dried over Na2SO4, concentrated and purified on silica gel (eluting with 0-50% EtOAc in hexane) to give the desired product (2.7 g, 85%). LCMS calculated for C11H13N2O2(M+H)+: m/z=205.1. Found: 205.1.
Workup
- stirringthe resulting suspension was stirred at room temperature for 2 hours
- customThe mixture was quenched with water
- extractionextracted with EtOAc
- dry with materialThe combined organic layers were dried over Na2SO4
- concentrationconcentrated
- custompurified on silica gel (eluting with 0-50% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-08d469cb094e4d53b55cf90120b6ec7d
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09062055B2
Reaction notes
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