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

HRID 16416Notes

Reaction equation

HRID 16416 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 (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

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