Iodine chloride → Methyl (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoate

HRID 377216Notes

Reaction equation

HRID 377216 reaction equation
[I:1]Cl.[CH2:3]([O:10][CH2:11][C@H:12]([C:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]([C:23]([CH3:29])([CH3:28])[C:24]([O:26][CH3:27])=[O:25])[CH:21]=2)[NH:16][C:15]=1[Si](CC)(CC)CC)[CH3:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO.CO.C1COCC1.F[B-](F)(F)F.[Ag+]>[CH2:3]([O:10][CH2:11][C@H:12]([C:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]([C:23]([CH3:29])([CH3:28])[C:24]([O:26][CH3:27])=[O:25])[CH:21]=2)[NH:16][C:15]=1[I:1])[CH3:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 24640Iodine chlorideHCID 15887216methyl (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-triethylsilyl-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoate

Product 1

HCID 15887217Methyl (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoateYield 84%

Reagents, catalysts & solvents 3

HCID 159722Silver tetrafluoroborateCatalystHCID 887MethanolSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of iodine monochloride (2.83 g, 17.4 mmol) in MeOH (25 mL) was added over approximately 0.5 h via pressure equalizing addition funnel to a vigorously stirred mixture of methyl (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-triethylsilyl-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoate (6.00 g, 13.4 mmol) and silver tetrafluroborate (3.39 g, 17.4 mmol) in MeOH/THF (1:2; 75 mL) at ) 0° C. After an additional 0.5 h, the reaction was quenched with 1 M Na2S2O3, warmed to room temperature and filtered through celite® washing copiously with ethyl acetate. The filtrate was concentrated under reduced pressure, poured into 1 M Na2S2O3 and extracted with ethyl acetate (x3). The combined organic extract was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (25% ethyl acetate/hexanes as eluent) to give the title compound as a colourless solid (5.54 g, 84%).

Workup

  1. additionaddition funnel
  2. customthe reaction was quenched with 1 M Na2S2O3
  3. filtrationfiltered through celite®
  4. washwashing copiously with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. additionpoured into 1 M Na2S2O3
  7. extractionextracted with ethyl acetate (x3)
  8. extractionThe combined organic extract
  9. washwas washed with brine
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by flash chromatography on silica gel (25% ethyl acetate/hexanes as eluent)

Sources & evidence

ORD record
ord-315b5799e455435881b358b4d18b4517
Source dataset
uspto-grants-2000_02
Patent number
US06025366

Reaction notes

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