Dimethylformamide → 4-Chloro-1H-pyrrolo[2,3-b]pyridine
Reaction equation
[NH:1]1[C:5]2=[N+:6]([O-])[CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.CN(C)C=O.CS([Cl:20])(=O)=O.[OH-].[Na+]>O>[Cl:20][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:1][CH:2]=[CH:3][C:4]=12Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 73 °C
Procedure
To a 50° C. pink solution of 1H-pyrrolo[2,3-b]pyridine 7-oxide (2.47 g, 0.0184 mol) in N,N-dimethylformamide (13.3 mL, 0.172 mol) was added methanesulfonyl chloride (4.0 mL, 0.052 mol). The pink color changed to orange. The mixture was heated to 73° C. for 2 h, and cooled to 40° C. Then 35 mL of water was added and the resulting suspension was cooled to 0° C. NaOH was added to adjust the pH of the mixture to ˜7. The mixture was filtered and washed with water (×3) to give 3.8 g of wet pale orange solid that was dried at 40° C. overnight to give 2.35 g (82.2% yield).
Workup
- temperaturecooled to 40° C
- temperaturethe resulting suspension was cooled to 0° C
- filtrationThe mixture was filtered
- washwashed with water (×3)
Sources & evidence
- ORD record
- ord-f17b2430e31c48e89cc685574e5542e4
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445488B2
Reaction notes
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