Dimethylcarbamoyl Chloride → HCID 18993299, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH:12]=[CH:13][NH:14]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[K+].[CH3:19][N:20]([CH3:24])[C:21](Cl)=[O:22].[NH4+].[Cl-]>C1COCC1.C(OCC)(=O)C>[CH3:19][N:20]([CH3:24])[C:21]([N:14]1[C:15]2[C:11](=[CH:10][CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:16]=2)[CH:12]=[CH:13]1)=[O:22]Participants
Procedure
To a 0° C. solution of 6-(4-fluorophenyl)indole (2.00 g, 9.48 mmol), prepared as described in WO 93/01813, in THF (50 mL) was added KOH (2.7 g, 47.4 mmol) in a single portion and the cold bath was removed. After stirring for 15 min at ambient temperature, dimethylcarbamoyl chloride (1.3 mL, 14.2 mmol) was added via syringe and the resulting brown suspension was stirred for 4 hours at ambient temperature. The reaction mixture was poured into a mixture of ethyl acetate and saturated aqueous NH4Cl and the layers were separated. The aqueous phase was extracted twice with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to afford 6-(4-fluorophenyl)indole-1-carboxylic acid dimethylamide as a brown solid which was used without further purification.
Workup
- customthe cold bath was removed
- stirringthe resulting brown suspension was stirred for 4 hours at ambient temperature
- customthe layers were separated
- extractionThe aqueous phase was extracted twice with ethyl acetate
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-a815ec5cabb549d292217d272ba6d6bc
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05486525
Reaction notes
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