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

HRID 389427Notes

Reaction equation

HRID 389427 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[C:3]=1[CH3:12].[I:13]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:13])=[C:4]2[C:3]=1[CH3:12]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 667605962-Chloro-3-methylfuro[2,3-c]pyridin-7-amine

Product 1

HCID 667606172-Chloro-4-iodo-3-methylfuro[2,3-c]pyridin-7-amineYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-chloro-3-methylfuro[2,3-c]pyridin-7-amine (1.0 g, 5.5 mmol) in MeCN (30 mL) was treated with N-iodosuccinimide (1.70 g, 7.52 mmol), added portionwise over a 5 min period. The mixture was stirred at RT for overnight. The reaction was quenched with 20% aqueous Na2S2O3 and stirred for 10 min. EtOAc (100 mL) was added and the phases separated. The organic phase was washed with 20% aqueous Na2S2O3, then water and finally with brine. After drying over Na2SO4, the organic extracts were filtered and concentrated in vacuo. The material was purified using flash chromatography (30% EtOAc:DCM) to afford 1.15 g (68%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 8.07 (s, 1H), 4.73 (br s, 2H), 2.33 (s, 3H).

Workup

  1. additionadded portionwise over a 5 min period
  2. customThe reaction was quenched with 20% aqueous Na2S2O3
  3. stirringstirred for 10 min
  4. additionEtOAc (100 mL) was added
  5. customthe phases separated
  6. washThe organic phase was washed with 20% aqueous Na2S2O3
  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-1f6ef8de700b4b779c877888723e8be1
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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