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

HRID 2264917Notes

Reaction equation

HRID 2264917 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:13]([CH2:14][CH2:15][O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[C:12]2[CH:11]=[CH:10][N:9]=[CH:8][C:7]=2[C:6]=1[NH:27][C:28]1[CH:33]=[CH:32][C:31]([Si](C)(C)C)=[CH:30][C:29]=1[F:38])=[O:4].[I:39]Cl>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[N:13]([CH2:14][CH2:15][O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[C:12]2[CH:11]=[CH:10][N:9]=[CH:8][C:7]=2[C:6]=1[NH:27][C:28]1[CH:33]=[CH:32][C:31]([I:39])=[CH:30][C:29]=1[F:38])=[O:4]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 595966283-(2-Fluoro-4-trimethylsilanyl-phenylamino)-1-(2-triisopropylsilanyloxy-ethyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid methyl ester

Product 1

HCID 595965243-(2-Fluoro-4-iodo-phenylamino)-1-(2-triisopropylsilanyloxy-ethyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid methyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 3-(2-fluoro-4-trimethylsilanyl-phenylamino)-1-(2-triisopropylsilanyloxy-ethyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid methyl ester (1.78 g, 3.20 mmol) in DCM (35 mL) was added iodine monochloride (1M in DCM, 6.40 mL) dropwise over 10 minutes. The mixture was stirred for 1 hour then quenched by the addition of saturated sodium thiosulphate solution. The solution was partitioned between ethyl acetate and an saturated solution of sodium hydrogencarbonate. The organic layer was separated, washed with water then brine, dried (Na2SO4), filtered and evaporated to give a residue. The residue was purified by flash chromatography (Si-PPC, cyclohexane:ethylacetate, gradient 100:0 to 0:100) to provide the title compound as a yellow oil (1.52 g, 79%). LCMS (method B): RT=3.47 min, M+H+=612.

Workup

  1. customthen quenched by the addition of saturated sodium thiosulphate solution
  2. customThe solution was partitioned between ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialbrine, dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give a residue
  9. customThe residue was purified by flash chromatography (Si-PPC, cyclohexane:ethylacetate, gradient 100:0 to 0:100)

Sources & evidence

ORD record
ord-5ae5dea626134fcda31ab6c9229740ed
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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