Iodine → HCID 67006217, compound

HRID 470848Notes

Reaction equation

HRID 470848 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.[Si:22]([O:29][CH2:30][C@@H:31]([NH:46][C:47]1[CH:52]=[CH:51][C:50]([C:53]#[N:54])=[C:49]([Cl:55])[C:48]=1[CH3:56])[C:32]([NH:34][NH:35][C:36](=O)[C:37]1[CH:42]=[CH:41][C:40]([C:43]#[N:44])=[CH:39][CH:38]=1)=[O:33])([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>C(Cl)Cl>[Si:22]([O:29][CH2:30][C@@H:31]([NH:46][C:47]1[CH:52]=[CH:51][C:50]([C:53]#[N:54])=[C:49]([Cl:55])[C:48]=1[CH3:56])[C:32]1[O:33][C:36]([C:37]2[CH:38]=[CH:39][C:40]([C:43]#[N:44])=[CH:41][CH:42]=2)=[N:35][N:34]=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 807IodineHCID 11776TriphenylphosphineHCID 67006839HCID 67006839, compound

Product 1

HCID 67006217HCID 67006217, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Polymer supported triphenylphosphine (1.5 g, 4.46 mmol) was diluted in 200 mL of DCM followed by addition of I2 (1.13 g, 4.46 mmol) and TEA (1.67 mL, 18.8 mmol) at 0° C. (R)-N′-(3-(tert-butyldimethylsilyloxy)-2-(3-chloro-4-cyano-2-methylphenylamino)propanoyl)-4-cyanobenzohydrazide (1.52 g, 2.97 mmol) in 200 ml DCM was added to the pre-cooled solution mixture of PPh3/I2/TEA system and stirred. The temperature was allowed to come to room temperature and stirred for additional 10 min. The reaction was quenched with 50 mL saturated sodium thiosulfate and the biphasic mixture was separated. The aqueous layer was extracted with EtOAc (3×40 mL) and the combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The resulting crude oil was purified by flash chromatography (SiO2) to provide the title compound (0.860 g, 59%). The crude material was used directly in the next step.

Workup

  1. customto come to room temperature
  2. stirringstirred for additional 10 min
  3. customThe reaction was quenched with 50 mL saturated sodium thiosulfate
  4. customthe biphasic mixture was separated
  5. extractionThe aqueous layer was extracted with EtOAc (3×40 mL)
  6. dry with materialthe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting crude oil was purified by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-163887db1ed44a60b2bc20736756f8f4
Source dataset
uspto-grants-2014_01
Patent number
US08629167B2

Reaction notes

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