Methyl chloroformate → 6-chloro-4-nitro-1H-pyrrolo[2,3-b]pyridine
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-])=[C:6]2[NH:11][CH:12]=[CH:13][C:5]=12)([O-:3])=[O:2].C[Si](C)(C)N[Si](C)(C)C.[Cl:23]C(OC)=O>C1COCC1>[Cl:23][C:8]1[N:7]=[C:6]2[NH:11][CH:12]=[CH:13][C:5]2=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Under an atmosphere of argon, 5.00 g (27.9 mmol) of 4-nitro-1H-pyrrolo[2,3-b]pyridine 7-oxide (from example XVI) and 11.8 ml (55.8 mmol) of hexamethyldisilazane are initially charged in 290 ml of THF. At room temperature, 10.8 ml (139.6 mmol) of methyl chloroformate are added. The solution is stirred at RT overnight. The reaction solution is filtered through a silica gel cartridge, and is then washed with DCM/methanol 10:1.
Workup
- filtrationThe reaction solution is filtered through a silica gel cartridge
- washis then washed with DCM/methanol 10:1
Sources & evidence
- ORD record
- ord-cd4d09d395a04def8707814160ffa2fb
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737153B2
Reaction notes
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