Iodine → HCID 67005931, compound

HRID 2388438Notes

Reaction equation

HRID 2388438 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.[Si:22]([O:29][C@H:30]([CH3:60])[C@@H:31]([NH:46][C:47]1[CH:52]=[CH:51][C:50]([C:53]#[N:54])=[C:49]([C:55]([F:58])([F:57])[F:56])[C:48]=1[CH3:59])[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][C@H:30]([CH3:60])[C@@H:31]([NH:46][C:47]1[CH:52]=[CH:51][C:50]([C:53]#[N:54])=[C:49]([C:55]([F:58])([F:56])[F:57])[C:48]=1[CH3:59])[C:32]1[O:33][C:36]([C:37]2[CH:42]=[CH:41][C:40]([C:43]#[N:44])=[CH:39][CH:38]=2)=[N:35][N:34]=1)([C:25]([CH3:26])([CH3:28])[CH3:27])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 807IodineHCID 11776TriphenylphosphineHCID 67006584HCID 67006584, compound

Product 1

HCID 67005931HCID 67005931, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triphenylphosphine (590 mg, 2.25 mmol) was dissolved in 25 mL of DCM followed by addition of I2 (571 mg, 2.25 mmol) and TEA (456 mg, 4.50 mmol) at 0° C. N′-((2R,3R)-3-(tert-butyldimethylsilyloxy)-2-(4-cyano-2-methyl-3-(trifluoromethyl)phenylamino)butanoyl)-4-cyanobenzohydrazide (630 mg, 1.13 mmol) in 25 mL DCM was added to the pre-cooled solution mixture of PPh3/I2/TEA system and stirred. The temperature was allowed to rise to room temperature and stirred for additional 10 min. The reaction was quenched with 50 mL saturated sodium thiosulfate and extract with EtOAc. The crude mixture was chromatographed to give the product (510 mg, 84%) 1H NMR(400 MHz, acetone-d6, δ in ppm): 8.23 (d, J=9 Hz, 2H), 8.04 (d, J=9 Hz, 2H), 7.67 (d, J=9 Hz, 1H), 7.27 (d, J=9 Hz, 1H), 5.94 (d, J=9 Hz, 1H), 5.19 (m, 1H), 4.74 (m, 1H), 2.39 (m, 3H), 1.48 (d, J=6 Hz, 3H), 0.81 (s, 9H), 0.12 (s, 3H), 0.00 (s, 3H).

Workup

  1. customto rise to room temperature
  2. stirringstirred for additional 10 min
  3. customThe reaction was quenched with 50 mL saturated sodium thiosulfate
  4. extractionextract with EtOAc
  5. customThe crude mixture was chromatographed

Sources & evidence

ORD record
ord-934b8c5613f2493fab7974f13927b729
Source dataset
uspto-grants-2012_09
Patent number
US08268872B2

Reaction notes

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