Sodium Iodide → 3-(2-Fluoro-4-iodo-phenylamino)-1-(2-methoxy-ethyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

HRID 2264912Notes

Reaction equation

HRID 2264912 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]([I:22])=[CH:18][C:17]=1[F:23])=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:33][CH2:34][O:35][CH3:36]>CN(C=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH2:33][CH2:34][O:35][CH3:36])[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:22])=[CH:18][C:17]=1[F:23])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 672119973-(2-fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 595965443-(2-Fluoro-4-iodo-phenylamino)-1-(2-methoxy-ethyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl esterYield 16.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-(2-Fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (234 mg, 0.55 mmol), potassium carbonate (91 mg, 0.66 mg), sodium iodide (103 mg, 0.69 mmol) and 1-bromo-2-methoxy-ethane (0.057 mL, 0.61 mmol) in DMF (5 mL) was stirred a 90° C. for 2 days. It was cooled to room temperature, diluted with water and extracted into ethyl acetate. The organic layer was separated then washed with water followed by brine, then dried (Na2SO4), filtered and concentrated to give a residue which was purified by flash chromatography (Si-PPC, ether:pentane, gradient 20:80 to 50:50) to provide the title compound as a yellow oil (44 mg, 16%). LCMS (method B): RT=2.56 min, M+H+=483.

Workup

  1. temperatureIt was cooled to room temperature
  2. extractionextracted into ethyl acetate
  3. customThe organic layer was separated
  4. washthen washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a residue which
  9. customwas purified by flash chromatography (Si-PPC, ether:pentane, gradient 20:80 to 50:50)

Sources & evidence

ORD record
ord-38635dd29b644b8fb3a36d26ff797a93
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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