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

HRID 2264924Notes

Reaction equation

HRID 2264924 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH3:15])[C:13]2[C:12]([Cl: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]([Cl: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 595965317-Chloro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 595966487-Chloro-3-(2-fluoro-4-iodo-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl esterYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 7-chloro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (3.25 g, 7.74 mmol) in DCM (50 mL) was added iodine monochloride (1M in DCM, 17.0 mL) dropwise over 15 minutes. The mixture was allowed to warm to ambient temperature then partitioned between ethyl acetate and a saturated solution of sodium thiosulphate. The organic layer was separated, washed with water then brine, dried (Na2SO4), filtered and evaporated to give a residue. The residue was triturated with diethyl ether to provide the title compound as a yellow solid (2.62 g, 73%). LCMS (method B): RT=3.95 min, M+H+=474.

Workup

  1. customthen partitioned between ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialbrine, dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue
  8. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-a942f57b14bc4cb28b1c92cbba40e102
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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