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 and 11.8 ml (55.8 mmol) of hexamethyldisilazane are initially charged in 290 ml of THF. At RT, 10.8 ml (140 mmol) of methyl chloroformate are added. The solution is stirred at RT overnight. The reaction solution is filtered through a silica gel cartridge, and the cartridge is washed with dichloromethane/methanol 10:1.
Workup
- filtrationThe reaction solution is filtered through a silica gel cartridge
- washthe cartridge is washed with dichloromethane/methanol 10:1
Sources & evidence
- ORD record
- ord-c437acc50e064b809657cfdfa9de6046
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329716B2
Reaction notes
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