Sodium Carbonate → 6-Chloro-2-iodothieno[2,3-b]pyridine

HRID 1465753Notes

Reaction equation

HRID 1465753 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[S:8][CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.C1C(=O)N([I:18])C(=O)C1.OS(C(F)(F)F)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>>[Cl:1][C:2]1[N:7]=[C:6]2[S:8][C:9]([I:18])=[CH:10][C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 62406Trifluoromethanesulfonic acidHCID 120273N-IodosuccinimideHCID 116368806-Chlorothieno(2,3-b)pyridine

Product 1

HCID 895251046-Chloro-2-iodothieno[2,3-b]pyridine

Procedure

To a flask charged with 6-Chlorothieno[2,3-b]pyridine (500 mg, 3.0 mmol) and a stir bar was added NIS (800 mg, 3.5 mmol) and Triflic acid (5 mL). The mixture was monitored by TLC and allowed to stir at RT for 4 hours. The reaction was poured into ice, neutralized with aqueous sodium carbonate, extracted with DCM, dried over sodium sulfate, concentrated and purified by flash chromatography (Hex: EtOAc gradient) to obtain the title product. LC-MS (IE, m/z): 296 [M+1]+.

Workup

  1. additionThe reaction was poured into ice
  2. extractionextracted with DCM
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by flash chromatography (Hex: EtOAc gradient)

Sources & evidence

ORD record
ord-100a5771ee614374aeaf1418aaaf0527
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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