Trimethylsilyl triflate → HCID 71484120, compound

HRID 921057Notes

Reaction equation

HRID 921057 reaction equation
C(O[I:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)OC(=O)C)(=O)C.[Si]([O:20][S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22])(C)(C)C.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1>>[F:25][C:24]([F:27])([F:26])[S:21]([O-:23])(=[O:22])=[O:20].[F:25][C:24]([F:27])([F:26])[S:21]([O-:23])(=[O:22])=[O:20].[C:10]1([I:5]([N+:33]2[CH:34]=[CH:35][C:30]([O:29][CH3:28])=[CH:31][CH:32]=2)[N+:33]2[CH:34]=[CH:35][C:30]([O:29][CH3:28])=[CH:31][CH:32]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 692784-MethoxypyridineHCID 76724Iodobenzene diacetate

Product 1

HCID 71484120HCID 71484120, compoundYield 97.3%

Procedure

Based on a reported procedure: All manipulations were carried out in a dry box under a N2 atmosphere. To (diacetoxyiodo)benzene (3.00 g, 9.31 mmol, 1.00 equiv) dissolved in CH2C12 (100 mL) in a round-bottom flask was added TMSOTf (4.14 g, 18.6 mmol, 2.00 equiv) dropwise over 1 minute at 23 ° C. 4-Methoxypyridine (2.03 g, 18.6 mmol, 2.00 equiv) in CH2C12 (15 mL) was added to the solution dropwise over 5 minutes. The reaction mixture was concentrate until a white solid was observed. To the reaction mixture was added 100 mL of Et2O and the resulting solid was collected on a frit. The solid was washed with Et2O (3 x 10 mL) and subsequently dried under vacuum to afford 6.52 g of the title compound as a colorless solid (97%). NMR Spectroscopy: c 1H NMR (500 MHz, CD3CN, 23 ° C., δ): 8.77 (d, J=7.5 Hz, 4H), 8.60 (d, J=8.5 Hz, 2H), 7.79 (t, J=7.5 Hz, 1H), 7.64 (t, J=8.5 Hz, 2H), 7.19 (d, J=7.5 Hz, 4H), 3.99 (s, 3H). 13C NMR (125 MHz, CD3CN, 23 ° C., δ): 172.1, 149.9, 136.1, 135.7, 134.2, 121.9 (q, J=319 Hz, triflate), 115.3, 58.5. 19F NMR (375 MHz, CD3CN, 23 ° C., δ): −77.5. Anal: calcd for C20H19F6IN2O8S2: C, 33.34; H, 2.66; N, 3.89; found: C, 33.05; H, 2.59; N, 3.73.

Workup

  1. customAll manipulations were carried out in a dry box under a N2 atmosphere
  2. concentrationThe reaction mixture was concentrate until a white solid
  3. additionTo the reaction mixture was added 100 mL of Et2O
  4. customthe resulting solid was collected on a frit
  5. washThe solid was washed with Et2O (3 x 10 mL)
  6. customsubsequently dried under vacuum

Sources & evidence

ORD record
ord-343a1101ec314d5db432dfb3644429fd
Source dataset
uspto-grants-2016_03
Patent number
US09273083B2

Reaction notes

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