Bromine → 3-bromo-4-nitro-1H-pyrrolo[2,3-b]pyridine

HRID 2240225Notes

Reaction equation

HRID 2240225 reaction equation
[Br:1]Br.[N+:3]([C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[NH:12][CH:13]=[CH:14][C:7]=12)([O-:5])=[O:4].C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:14]1[C:7]2[C:8](=[N:9][CH:10]=[CH:11][C:6]=2[N+:3]([O-:5])=[O:4])[NH:12][CH:13]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 6392484-Nitro-7-azaindole

Product 1

HCID 247295713-bromo-4-nitro-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., 316 μl (6.13 mmol) of bromine are added dropwise to a solution of 1.00 g (6.13 mmol) of 4-nitro-1H-pyrrolo[2,3-b]pyridine (Antonini, Ippolito; Claudi, Francesco; Cristalli, Gloria; Franchetti, Palmarisa; Grifantini, Mario; Martelli, Sante; J. Med. Chem. 1982, 25, 1258-1261.) in 50 ml of dichloromethane. After 1 h of stirring at 0° C. and 1 h of stirring at room temperature, the solution is poured onto a mixture of ice and saturated sodium bicarbonate solution. The mixture is then extracted twice with dichloromethane. The combined organic phases are dried with sodium sulfate, and the solvent is removed under reduced pressure. The residue is taken up in a mixture of cyclohexane/ethyl acetate and the precipitate formed is filtered off.

Workup

  1. stirringof stirring at room temperature
  2. extractionThe mixture is then extracted twice with dichloromethane
  3. dry with materialThe combined organic phases are dried with sodium sulfate
  4. customthe solvent is removed under reduced pressure
  5. additionThe residue is taken up in a mixture of cyclohexane/ethyl acetate
  6. customthe precipitate formed
  7. filtrationis filtered off

Sources & evidence

ORD record
ord-3118c234584b4982b2280bbdcb94f4ec
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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