Sodium Bicarbonate → 4-Chloro-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine
Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]2[N:26](S(C3C=CC(C)=CC=3)(=O)=O)[CH:27]=[C:28]([C:29]([F:32])([F:31])[F:30])[C:21]=12.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]2[NH:26][CH:27]=[C:28]([C:29]([F:30])([F:31])[F:32])[C:21]=12Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
52.3 g (200 mmol) of tetra-n-butylammonium fluoride are added to a solution of 30 g (80.0 mmol) of 4-chloro-1-(toluene-4-sulphonyl)-3-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine in 250 ml of absolute THF and the mixture is stirred at 20° C. for 20 minutes. On completion of conversion (TLC monitoring), the mixture is admixed with 300 ml of saturated NaHCO3 solution and subsequently extracted three times with 500 ml each time of ethyl acetate. The combined organic phases are washed with saturated NaCl solution, dried over MgSO4 and freed of volatile constituents in a water-jet vacuum. Purification of the crystalline crude product by chromatography through silica gel (CH2Cl2: MeOH=30:1) results in 13.1 g (59.5 mmol; 74%) of 4-chloro-3-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine as a beige solid.
Workup
- extractionsubsequently extracted three times with 500 ml each time of ethyl acetate
- washThe combined organic phases are washed with saturated NaCl solution
- dry with materialdried over MgSO4
- customPurification of the crystalline crude product by chromatography through silica gel (CH2Cl2: MeOH=30:1)
Sources & evidence
- ORD record
- ord-ba533b2943a644059e1d0cc260235337
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07528146B2
Reaction notes
Loading…