Iodine chloride → 7-Fluoro-3-(2-fluoro-4-iodo-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

HRID 2264933Notes

Reaction equation

HRID 2264933 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH3:15])[C:13]2[C:12]([F:16])=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:17][C:18]1[CH:23]=[CH:22][C:21]([Si](C)(C)C)=[CH:20][C:19]=1[F:28])=[O:5])[CH3:2].[I:29]Cl>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH3:15])[C:13]2[C:12]([F:16])=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:17][C:18]1[CH:23]=[CH:22][C:21]([I:29])=[CH:20][C:19]=1[F:28])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 595965847-Fluoro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 595964347-Fluoro-3-(2-fluoro-4-iodo-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl esterYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 7-fluoro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (1.0 g, 2.48 mmol) in DCM (25 mL) was added iodine monochloride (1M in DCM, 4.96 mmol, 4.96 mL) dropwise. The mixture was stirred cold for 30 minutes then quenched by the addition of a saturated solution of sodium thiosulphate. The organic layer was separated, washed with a saturated solution of sodium thiosulphate, then dried (Na2SO4), filtered and evaporated to give a residue. The residue was triturated with diethyl ether to provide the title compound as a beige solid (805 mg, 71%). LCMS (method B): RT=3.52 min, M+H+ 458.

Workup

  1. customthen quenched by the addition of a saturated solution of sodium thiosulphate
  2. customThe organic layer was separated
  3. washwashed with a saturated solution of sodium thiosulphate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue
  8. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-f1643a97c05c4ee5803563195cc10d0a
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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