N-Iodosuccinimide → 4-Iodo-2-(isoquinolin-5-yl)furo[2,3-c]pyridin-7-amine

HRID 389432Notes

Reaction equation

HRID 389432 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([C:11]3[O:20][C:14]4=[C:15]([NH2:19])[N:16]=[CH:17][CH:18]=[C:13]4[CH:12]=3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C1C(=O)N([I:28])C(=O)C1>CN(C=O)C>[I:28][C:18]1[CH:17]=[N:16][C:15]([NH2:19])=[C:14]2[O:20][C:11]([C:6]3[CH:7]=[CH:8][CH:9]=[C:10]4[C:5]=3[CH:4]=[CH:3][N:2]=[CH:1]4)=[CH:12][C:13]=12

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 66760648HCID 66760648, compound

Product 1

HCID 667594744-Iodo-2-(isoquinolin-5-yl)furo[2,3-c]pyridin-7-amineYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-(isoquinolin-5-yl)furo[2,3-c]pyridin-7-amine (5.6 g, 21.5 mmol) in DMF (250 mL) was treated with NIS (8.73 g, 38.6 mmol) added portionwise with stirring over a period of 5 min. The mixture was stirred at RT overnight. The reaction was quenched with aqueous Na2S2O3, diluted with EtOAc (1 L) and the phases separated. The organic layer was concentrated in vacuo. Water was added to the residue resulting in the formation of a solid after stirring overnight. The material was collected by filtration and the filter cake was washed with water and hexane. The material was dried over P2O5 at 50° C. in a high vacuum oven to provide 7.0 g (84%) of the title compound as a brown solid. 1H NMR (300 MHz, CDCl3+CD3OD): δ 6.92 (s, 1H), 7.70 (t, J=8.1 Hz, 1H), 7.98 (s, 1H), 8.11 (t, J=7.5 Hz, 2H), 8.20 (d, J=6.0 Hz, 1H), 8.53 (d, J=6.0 Hz, 1H), 9.24 (s, 1H).

Workup

  1. additionadded portionwise
  2. stirringThe mixture was stirred at RT overnight
  3. customThe reaction was quenched with aqueous Na2S2O3
  4. additiondiluted with EtOAc (1 L)
  5. customthe phases separated
  6. concentrationThe organic layer was concentrated in vacuo
  7. additionWater was added to the residue
  8. customresulting in the formation of a solid
  9. stirringafter stirring overnight
  10. filtrationThe material was collected by filtration
  11. washthe filter cake was washed with water and hexane
  12. dry with materialThe material was dried over P2O5 at 50° C. in a high vacuum oven

Sources & evidence

ORD record
ord-f1daeb7278584e17b2b50f8c174f5cad
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

Loading…