N-Iodosuccinimide → 2-Chloro-4-iodofuro[2,3-c]pyridin-7-amine

HRID 389423Notes

Reaction equation

HRID 389423 reaction equation
[Cl:1][C:2]1[O:11][C:5]2=[C:6]([NH2:10])[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1.[I:12]N1C(=O)CCC1=O>CC#N>[Cl:1][C:2]1[O:11][C:5]2=[C:6]([NH2:10])[N:7]=[CH:8][C:9]([I:12])=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 66759887HCID 66759887, compound

Product 1

HCID 667601342-Chloro-4-iodofuro[2,3-c]pyridin-7-amineYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-chlorofuro[2,3-c]pyridin-7-amine (9.0 g, 53.8 mmol) in MeCN (250 mL) was treated with N-iodosuccinimide (18.2 g, 80.8 mmol) added portionwise over a 5-10 min period. The mixture was stirred at RT for 16 h. The reaction was then quenched with 20% aqueous Na2S2O3 and stirred for 10 min. EtOAc (200 mL) was added and the phases separated. The organic phase was washed with 20% aqueous Na2S2O3 (50 mL), then water (2×100 mL) and finally with brine. After drying over Na2SO4, the organic extracts were filtered and concentrated in vacuo. The material was purified using flash chromatography (25% EtOAc:hexane) to afford 12.6 g (80%) of the title compound. 1H NMR (300 MHz CDCl3): δ 4.76 (br. s, 2H), 6.49 (s, 1H), 8.05 (s, 1H).

Workup

  1. additionadded portionwise over a 5-10 min period
  2. customThe reaction was then quenched with 20% aqueous Na2S2O3
  3. stirringstirred for 10 min
  4. additionEtOAc (200 mL) was added
  5. customthe phases separated
  6. washThe organic phase was washed with 20% aqueous Na2S2O3 (50 mL)
  7. dry with materialAfter drying over Na2SO4
  8. filtrationthe organic extracts were filtered
  9. concentrationconcentrated in vacuo
  10. customThe material was purified

Sources & evidence

ORD record
ord-ff248bc9a14a42ac91a745523930d774
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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