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

HRID 2240209Notes

Reaction equation

HRID 2240209 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 argon atmosphere, 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-9fc6976530564e3ebbadc612ecef47ef
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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