Methanesulfonyl chloride → 4-Chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine

HRID 1696202Notes

Reaction equation

HRID 1696202 reaction equation
[N+](C1C=C[N+]([O-])=C2NC=CC=12)([O-])=O.[N+:14]([C:17]1[C:25]2[C:20](=[N+:21]([O-])[CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)([O-:16])=[O:15].CS([Cl:31])(=O)=O>CN(C)C=O>[Cl:31][C:24]1[CH:23]=[CH:22][N:21]=[C:20]2[NH:19][CH:18]=[C:17]([N+:14]([O-:16])=[O:15])[C:25]=12

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 178526747HCID 178526747, compoundHCID 178526852HCID 178526852, compound

Product 1

HCID 247295694-Chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of a 2:1 mixture (589.8 mg) of 4-nitro-1H-pyrrolo-[2,3-b]pyridine 7-oxide and 3-nitro-1H-pyrrolo[2,3-b]pyridine-7-oxide in N,N-dimethylformamide (6 ml) was added dropwise methanesulfonyl chloride (0.68 ml) at 65° C. The reaction mixture was stirred at 65° C. for 2 hours. The reaction mixture was quenched with water (30 ml) under ice cooling, and neutralized (pH ˜6.5) with 20% NaOH solution. The resulting precipitates were collected by filtration, dried in vacuo at 40° C., and washed with EtOAc to give 4-chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine (172.8 mg) as a brown solid.

Workup

  1. customThe reaction mixture was quenched with water (30 ml) under ice cooling
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. customdried in vacuo at 40° C.
  5. washwashed with EtOAc

Sources & evidence

ORD record
ord-3323f3aa8e9c4f79a838f55180926f97
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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