Methyl chloroformate → 6-chloro-4-nitro-1H-pyrrolo[2,3-b]pyridine

HRID 2192146Notes

Reaction equation

HRID 2192146 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]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 13838HexamethyldisilazaneHCID 178526747HCID 178526747, compound

Product 1

HCID 179793386-chloro-4-nitro-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. filtrationThe reaction solution is filtered through a silica gel cartridge
  2. 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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