Reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:8]([C:11]([OH:13])=O)=[CH:7][CH:6]=[CH:5][C:4]=2[NH:3]1.[Cl:14][C:15]1[CH:16]=[C:17]([NH2:23])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[Cl:14][C:15]1[CH:16]=[C:17]([NH:23][C:11]([C:8]2[C:9]3[CH2:10][C:2](=[O:1])[NH:3][C:4]=3[CH:5]=[CH:6][CH:7]=2)=[O:13])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 2-oxo-2,3-dihydro-1H-indole-4-carboxylic acid (200 mg, 1.13 mmol) and 3-chloro-4-methoxy-phenylamine (178 mg, 1.13 mmol) in dimethylformamide (15 mL) at room temperature benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent 997 mg, 2.26 mmol) was added followed by 4-dimethylaminopyridine (206 mg, 1.69 mmol). The mixture was stirred at room temperature for 72 hours. The reaction was then diluted with ethyl acetate (300 mL), washed with saturated sodium bicarbonate solution (100 mL), water, 2N hydrochloric acid (100 mL), water (3×200 mL) and brine, dried (over magnesium sulfate) and concentrated. The residue was triturated with ethyl acetate to give 2-oxo-2,3-dihydro-1H-indole-4-carboxylic acid (3-chloro-4-methoxy-phenyl)-amide as a tarnish-pink solid.
Workup
- washwashed with saturated sodium bicarbonate solution (100 mL), water, 2N hydrochloric acid (100 mL), water (3×200 mL) and brine
- dry with materialdried (over magnesium sulfate)
- concentrationconcentrated
- customThe residue was triturated with ethyl acetate
Sources & evidence
- ORD record
- ord-817f487d9a8347ca899d29c8e426e9bb
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06706709B2
Linked notes
Loading…