Iodine → HCID 24805984, compound

HRID 1889596Notes

Reaction equation

HRID 1889596 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.II.CCN(C(C)C)C(C)C.[Si:31]([O:38][C@@H:39]1[C@@H:43]([CH2:44][O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])[O:42][C@@H:41]([N:53]2[C:62]3[N:61]=[CH:60][N:59]=[C:57]([OH:58])[C:56]=3[N:55]=[CH:54]2)[CH2:40]1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32].[CH:63]1[CH:64]=[CH:65][C:66]2[N:71](O)[N:70]=[N:69][C:67]=2[CH:68]=1>C(Cl)Cl>[N:69]1([O:58][C:57]2[C:56]3[N:55]=[CH:54][N:53]([C:62]=3[N:61]=[CH:60][N:59]=2)[C@@H:41]2[O:42][C@H:43]([CH2:44][O:45][Si:46]([C:49]([CH3:50])([CH3:51])[CH3:52])([CH3:47])[CH3:48])[C@@H:39]([O:38][Si:31]([C:34]([CH3:36])([CH3:37])[CH3:35])([CH3:33])[CH3:32])[CH2:40]2)[C:67]2[CH:68]=[CH:63][CH:64]=[CH:65][C:66]=2[N:71]=[N:70]1

Participants

7

Reactant 5

HCID 807IodineHCID 11776TriphenylphosphineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 178455234HCID 178455234, compound

Product 1

HCID 24805984HCID 24805984, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 mL round-bottom flask equipped with a stirring bar were placed PPh3 (0.823 g, 3.138 mmol) and I2 (0.800 g, 3.152 mmol) in dry CH2Cl2 (11.0 mL) and the mixture was stirred at room temperature for 20 min. DIPEA (1.5 mL, 8.62 mmol) and 3′,5′-bis-O-(tert-butyldimethylsilyl)-2′-deoxyinosine (1a) (0.500 g, 1.040 mmol) were added, and the mixture was allowed to stir at room temperature for 26 h. To this mixture was added HOBT (0.211 g, 1.561 mmol) and the reaction was allowed to continue and was complete in 22 h. The crude material was evaporated and chromatographic purification (SiO2, elution with 20% EtOAc in hexanes) afforded 0.578 g (93%) of compound 26 as a beige foam.

Workup

  1. customIn a 50 mL round-bottom flask equipped with a stirring bar
  2. stirringto stir at room temperature for 26 h
  3. waitwas complete in 22 h
  4. customThe crude material was evaporated
  5. customchromatographic purification (SiO2, elution with 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d690c12edbe54b9caf021c63867dbee7
Source dataset
uspto-grants-2013_08
Patent number
US08501931B2

Reaction notes

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