Iodine chloride → 3-(2-fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

HRID 2264905Notes

Reaction equation

HRID 2264905 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:14][C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([Si](C)(C)C)=[CH:18][C:17]=1[F:26])=[O:5])[CH3:2].[I:27]Cl>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[NH:14][C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([I:27])=[CH:18][C:17]=1[F:26])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 595966623-(2-Fluoro-4-trimethylsilanyl-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 672119973-(2-fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (−10° C.) solution of 3-(2-fluoro-4-trimethylsilanyl-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (140 mg, 0.343 mmol) in DCM (5 mL) was added iodine monochloride (1M in DCM, 0.90 mL) dropwise over 10 minutes. On complete addition the mixture was allowed to stir at ambient temperature for 20 minutes then quenched by the addition of saturated sodium thiosulphate solution (3 mL). The solution was partitioned between DCM (50 mL) and water (10 mL). The organic layer was separated, dried (Na2SO4), filtered and evaporated to give a yellow solid. The solid was triturated with diethyl ether, filtered and left to air dry to provide the title compound as a yellow solid (148 mg, 85%). LCMS (method B): RT=2.37 min, M+H+=426.

Workup

  1. additionOn complete addition the mixture
  2. customthen quenched by the addition of saturated sodium thiosulphate solution (3 mL)
  3. customThe solution was partitioned between DCM (50 mL) and water (10 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give a yellow solid
  9. customThe solid was triturated with diethyl ether
  10. filtrationfiltered
  11. waitleft to air
  12. customdry

Sources & evidence

ORD record
ord-49216c1edd6e4416a0ee2aec4d647599
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

Loading…