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

HRID 588412Notes

Reaction equation

HRID 588412 reaction equation
[CH3:1][C:2]1[NH:10][C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1.[I:11]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[I:11][C:3]1[C:4]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[NH:10][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 124075052-Methyl-1H-pyrrolo(2,3-c)pyridine

Product 1

HCID 674185123-iodo-2-methyl-1H-pyrrolo[2,3-c]pyridineYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Methyl-1H-pyrrolo[2,3-c]pyridine (100 mg, 0.76 mmol) was dissolved in CHCl3 (5 mL), N-iodosuccinimide (179 mg, 0.79 mmol) was added and the reaction mixture was stirred for 2 h. The reaction mixture was quenched with 1 M aq sodium thiosulphate (5 mL) and the CHCl3 was removed in vacuo. The reaction mixture was partitioned between sat aq NaHCO3 (40 mL) and EtOAc (40 mL). The aqueous layer was extracted with EtOAc (40 mL) and the combined organic fractions were washed with sat aq NaHCO3 (50 mL) and brine (50 mL), dried (MgSO4) and concentrated in vacuo to give the title compound as a cream solid (179 mg, 92%). LCMS (ES+): 258.9 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with 1 M aq sodium thiosulphate (5 mL)
  2. customthe CHCl3 was removed in vacuo
  3. customThe reaction mixture was partitioned
  4. extractionThe aqueous layer was extracted with EtOAc (40 mL)
  5. washthe combined organic fractions were washed with sat aq NaHCO3 (50 mL) and brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0bc03b6cdbca44099e42bb0342e9bb07
Source dataset
uspto-grants-2016_01
Patent number
US09227967B2

Reaction notes

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