Cesium carbonate → 6-Acetyl-3-(2,4-dichlorophenyl)-9-difluoromethyl-1-methyl-1,9-dihydropyrido[2,3-b]indol-2-one
Reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]1[N:13]([CH3:26])[C:14](=[O:25])[C:15]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[CH:16][C:7]2=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:34]([F:39])([F:38])C([O-])=O.[Na+]>CN(C=O)C.O>[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:34]([F:39])[F:38])[C:8]1[N:13]([CH3:26])[C:14](=[O:25])[C:15]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[CH:16][C:7]2=1)(=[O:3])[CH3:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
460 mg (1.19 mmol) of compound from preparation 1.9A, 6-acetyl-3-(2,4-dichlorophenyl)-1-methyl-1,9-dihydro-2H-pyrido[2,3-b]indol-2-one, are dissolved in 7 ml of DMF and 2 ml of water. 543 mg (1.67 mmol) of caesium carbonate and 419 mg (2.75 mmol) of sodium chlorodifluoroacetate are added. The mixture is heated at 100° C. for 48 hours. It is allowed to return to ambient temperature. The reaction medium is poured into water, and the precipitate formed is filtered off and washed with water. The product is taken up in an EtOAc/MeOH mixture and adsorbed onto silica. Purification is carried out on a silica column, elution being carried out with a 50/50 EtOAc/cyclohexane mixture and then with EtOAc.
Workup
- customto return to ambient temperature
- customthe precipitate formed
- filtrationis filtered off
- washwashed with water
- customPurification
- washis carried out on a silica column, elution
Sources & evidence
- ORD record
- ord-22fa2a0fceb442cc94cb2bff89a8dd53
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063061B2
Reaction notes
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