N-Iodosuccinimide → 4-Chloro-3-iodo-1H-pyrrolo[3,2-c]pyridine

HRID 69319Notes

Reaction equation

HRID 69319 reaction equation
[I:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:15]2[CH:16]=[CH:17][NH:18][C:14]=2[CH:13]=[CH:12][N:11]=1>CN(C)C=O>[Cl:9][C:10]1[C:15]2[C:16]([I:1])=[CH:17][NH:18][C:14]=2[CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 141143844-chloro-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 534128394-Chloro-3-iodo-1H-pyrrolo[3,2-c]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Iodosuccinimide (1.3 g, 5.8 mmol) was added to a 0° C. solution of 4-chloro-1H-pyrrolo[3,2-c]pyridine (0.60 g, 3.9 mmol) in N,N-dimethylformamide (10 mL). The reaction mixture was stirred at room temperature for 18 hours, whereupon it was concentrated in vacuo. Purification via silica gel chromatography (0% to 50% ethyl acetate in petroleum ether) afforded the product as a yellow solid. Yield: 900 mg, 3.2 mmol, 82%. 1H NMR (400 MHz, CDCl3) δ 8.10 (d, J=5.5 Hz, 1H), 7.42 (d, J=2.5 Hz, 1H), 7.34 (d, J=5.8 Hz, 1H).

Workup

  1. concentrationwas concentrated in vacuo
  2. customPurification via silica gel chromatography (0% to 50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-6f805d154a414f82bf9bad95d6ebd9ef
Source dataset
uspto-grants-2014_09
Patent number
US08822494B2

Reaction notes

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