Sodium Iodide → HCID 67412505, compound

HRID 222309Notes

Reaction equation

HRID 222309 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[CH:14]=[C:15](Br)[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.[I-:19].[Na+]>[Cu]I>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[CH:14]=[C:15]([I:19])[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 159808187-Bromo-3-chloro-5H-benzo[4,5]cyclohepta[1,2-B]pyridin-5-one

Product 1

HCID 67412505HCID 67412505, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

A sealed tube was charged with 3-chloro-7-bromo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (1.0 g, 3.1 mmol), CuI (59 mg, 0.31 mmol), and sodium iodide (0.94 g, 6.2 mmol). The tube was evacuated and backfilled with argon three times. Fully degassed dioxane (8 mL) was added. The tube was sealed, placed in an oil bath at 110° C., and stirred rapidly for 24 hours. Upon completion, the reaction mixture was cooled and quenched via the addition of 20 mL of a 30% aqueous ammonia solution, poured into 80 mL of water, and extracted three times with 150 mL dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered, concentrated in vacuo, and purified via flash chromatography (silica, 0-100% ethyl acetate/hexanes) to afford the title compound. 1H NMR (600 MHz, d6-DMSO) δ 8.99 (d, 1H), 8.43 (d, 1H), 8.39 (d, 1H), 8.16 (dd, 1H), 7.60 (d, 1H), 7.42 (d, 1H), 7.32 (d, 1H). LRMS (APCI) calc'd for (C14H8ClINO) [M+H]+, 367.9; found 367.9.

Workup

  1. customThe tube was evacuated
  2. additionFully degassed dioxane (8 mL) was added
  3. customThe tube was sealed
  4. customplaced in an oil bath at 110° C.
  5. temperatureUpon completion, the reaction mixture was cooled
  6. customquenched via the addition of 20 mL of a 30% aqueous ammonia solution
  7. additionpoured into 80 mL of water
  8. extractionextracted three times with 150 mL dichloromethane
  9. dry with materialThe combined organic phases were dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. custompurified via flash chromatography (silica, 0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c643cac603b14046b411ecf7aa3170ec
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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