N-bromobutanimide → 3,4-Dibromo-1H-pyrrolo[2,3-b]pyridine

HRID 330993Notes

Reaction equation

HRID 330993 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.C1C(=O)N([Br:18])C(=O)C1>C(Cl)Cl>[Br:18][C:10]1[C:3]2[C:4](=[N:5][CH:6]=[CH:7][C:2]=2[Br:1])[NH:8][CH:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 222736434-Bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 247295603,4-Dibromo-1H-pyrrolo[2,3-b]pyridineYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-bromo-1H-pyrrolo[2,3-b]pyridine (1.00 g, 5.08 mmol) and NBS (0.918 g, 5.16 mmol) in DCM (20.0 mL) was stirred at 0° C. for 1.5 hour. The resulting suspension was filtered, washed with DCM, residue collected, dried in a 50° C. oven overnight to afford the title compound (1.014 g). LCMS (A): m/z (M+H)+ 277, C7H4Br2N2 requires 276 (basic).

Workup

  1. filtrationThe resulting suspension was filtered
  2. washwashed with DCM, residue
  3. customcollected
  4. customdried in a 50° C. oven overnight

Sources & evidence

ORD record
ord-6fdbfeff5fef4ede9cd78247ca27ff8a
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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