7-Azaindole N-oxide 3-chlorobenzoate → 4-Chloro-1H-pyrrolo[2,3-b]pyridine
Reaction equation
[Cl:1]C1C=C(C=CC=1)C([O-])=O.O[N+:12]1[CH:17]=[CH:16][CH:15]=[C:14]2[CH:18]=[CH:19][NH:20][C:13]=12>O=P(Cl)(Cl)Cl>[Cl:1][C:15]1[CH:16]=[CH:17][N:12]=[C:13]2[NH:20][CH:19]=[CH:18][C:14]=12Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
POCl3 (10 mL) was added to 7-hydroxy-1H-pyrrolo[2,3-b]pyridin-7-ium 3-chlorobenzoate (1.0 g, 3.4 mmol). The resulting mixture was heated to 90° C. for 18 hours. The mixture was then cooled to room temperature and concentrated. The resulting residue was diluted with acetonitrile (“ACN”; 3 mL) and water (3 mL). The pH was adjusted with 50% NaOH to a pH of 9. The resulting solid was filtered and washed with water. The solid was then washed with DCM to give 4-chloro-1H-pyrrolo[2,3-b]pyridine (0.30 g, 57% yield).
Workup
- temperatureThe mixture was then cooled to room temperature
- concentrationconcentrated
- additionThe resulting residue was diluted with acetonitrile (“ACN”; 3 mL) and water (3 mL)
- filtrationThe resulting solid was filtered
- washwashed with water
- washThe solid was then washed with DCM
Sources & evidence
- ORD record
- ord-666d3b88f9e1437d849098ac5f43ad19
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841304B2
Reaction notes
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