N-Iodosuccinimide → 5-(2-fluorophenyl)-3-iodo-1H-pyrrolo[3,2-b]pyridine

HRID 1529343Notes

Reaction equation

HRID 1529343 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[CH:14]=[CH:15][NH:16][C:11]2=[CH:10][CH:9]=1.C1C(=O)N([I:24])C(=O)C1>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[C:14]([I:24])=[CH:15][NH:16][C:11]2=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 679599645-(2-fluorophenyl)-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 679597655-(2-fluorophenyl)-3-iodo-1H-pyrrolo[3,2-b]pyridineYield 73%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 5-(2-fluorophenyl)-1H-pyrrolo[3,2-b]pyridine (199 mg, 0.938 mmol) in THF (10 mL) was treated with n-iodosuccinimide (232 mg, 1.031 mmol, Alfa-Aesar). The reaction was stirred at 23° C. under N2. After 45 min, the solution was diluted with EtOAc (75 mL) and washed with brine (50 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluent: 15-30% EtOAc/hexane), affording 5-(2-fluorophenyl)-3-iodo-1H-pyrrolo[3,2-b]pyridine (231 mg, 73%). MS (ESI, pos. ion) m/z: 339.1 (M+1).

Workup

  1. washwashed with brine (50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. custompurified by silica gel chromatography (eluent: 15-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-167bf2296d624b7495d44142db4c819e
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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