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

HRID 609868Notes

Reaction equation

HRID 609868 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 tetrafluoroborate (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 1M Na2S2O3, warmed to room temperature and filtered through celite® washing copiously with ethyl acetate. The filtrate was concentrated under reduced pressure, poured into 1M Na2S2O3 and extracted with ethyl acetate (×3). 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 1M Na2S2O3
  3. filtrationfiltered through celite®
  4. washwashing copiously with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. additionpoured into 1M Na2S2O3
  7. extractionextracted with ethyl acetate (×3)
  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-57c813fd6a964044bf284b0c02f3f42c
Source dataset
uspto-grants-1999_12
Patent number
US05998432

Reaction notes

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