N-bromobutanimide → HCID 67353647, compound

HRID 1478903Notes

Reaction equation

HRID 1478903 reaction equation
[CH2:1]([N:3]1[C:11]2[CH:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[N:8]=[CH:7][C:6]=2[CH:5]=[CH:4]1)[CH3:2].C1C(=O)N([Br:23])C(=O)C1>C(Cl)Cl>[Br:23][C:5]1[C:6]2[CH:7]=[N:8][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:11]=2[N:3]([CH2:1][CH3:2])[CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67354512HCID 67354512, compound

Product 1

HCID 67353647HCID 67353647, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of methyl 1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (IF, 700 mg, 3.43 mmol) in DCM (5 ml) was added NBS (610 mg, 3.43 mmol). The reaction mixture was stirred at room temperature for 10 min. The reaction mixture was concentrated in vacuo and purified by chromatography (SiO2, EtOAc) to give methyl 3-bromo-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (3A, 950 mg, 3.36 mmol, 98% yield) as a white powder. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.52 (t, J=7.33 Hz, 3 H) 4.04 (s, 3 H) 4.25 (q, J=7.33 Hz, 2 H) 7.33 (s, 1 H) 8.22 (d, J=0.76 Hz, 1 H) 8.92 (d, J=1.01 Hz, 1 H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-3e9efdeaf122484fae22845a2d1769c4
Source dataset
uspto-grants-2016_08
Patent number
US09403819B2

Reaction notes

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