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

HRID 2264899Notes

Reaction equation

HRID 2264899 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH3:15])[C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([Si](C)(C)C)=[CH:19][C:18]=1[F:27])=[O:5])[CH3:2].[I:28]Cl>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH3:15])[C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([I:28])=[CH:19][C:18]=1[F:27])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 595964973-(2-Fluoro-4-trimethylsilanyl-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 595965873-(2-Fluoro-4-iodo-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(2-fluoro-4-trimethylsilanyl-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (37.0 g, 96.0 mmol) in CH2Cl2 (500 mL) was cooled to 0-5° C. and treated dropwise with iodine monochloride solution (211 mL, 1M in CH2Cl2). The mixture was allowed to warm and stirring continued for 1 hour. The solution was washed with aqueous sodium thiosulfate solution, dried (MgSO4) and evaporated in vacuo. The resultant residue was triturated with ethyl acetate to give the title compound (21.8 g, 52%) as a yellow solid. LCMS (method B): RT=2.48 min, M+H+=440.

Workup

  1. temperatureto warm
  2. washThe solution was washed with aqueous sodium thiosulfate solution
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe resultant residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-4f9683a1d6f44084b94d4d6b6ecbc133
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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