Trifluoroacetic acid → HCID 135465577, compound

HRID 853666Notes

Reaction equation

HRID 853666 reaction equation
[CH:1]([O:14][C:15]1[C:24]2[N:23]=[CH:22][CH:21]=[N:20][C:19]=2[C:18]([O:25]C)=[C:17]2[C:27](=[O:39])[N:28]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[C:29](=[O:30])[C:16]=12)(C1C=CC=CC=1)C1C=CC=CC=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:38][C:35]1[CH:34]=[CH:33][C:32]([CH2:31][N:28]2[C:27](=[O:39])[C:17]3[C:16](=[C:15]([O:14][CH3:1])[C:24]4[N:23]=[CH:22][CH:21]=[N:20][C:19]=4[C:18]=3[OH:25])[C:29]2=[O:30])=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58928688HCID 58928688, compound

Product 1

HCID 135465577HCID 135465577, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a flask containing 5-benzhydryloxy-7-(4-fluoro-benzyl)-9-methoxy-pyrrolo[3,4-g]quinoxaline-6,8-dione 246 (10 mg, 0.019 mmol, 1 equiv.) was added CH2Cl2 (1 mL) and under a nitrogen atmosphere was added triethylsilane (200 μL) followed by trifluoroacetic acid (200 μL). The reaction was allowed to stir for 1.5 hours and concentrated in vacuo until thoroughly dried. To the oil was added Hexanes/Ethyl ether (20 mL, 1/1 ratio) and sonicated. The resulting solid was filtered, washed in hexanes and air dried to give 7-(4-fluoro-benzyl)-5-hydroxy-9-methoxy-pyrrolo[3,4-g]quinoxaline-6,8-dione 249 (67%, 4.6 mg, 0.015 mmol). 1H NMR (300 MHz) CDCl3 δ 9.07 (d, J=1.8 Hz, 1 H), 8.97 (d, J=1.8 Hz, 1 H), 7.23-7.27 (m, 2 H), 6.96-7.05 (s, 2 H), 4.87 (s, 2 H), 4.46 (s, 3 H). 19F NMR (300 MHz) CDCl3 δ 62.77 MS: 354.0 (M+1)

Workup

  1. concentrationconcentrated in vacuo
  2. customuntil thoroughly dried
  3. additionTo the oil was added Hexanes/Ethyl ether (20 mL, 1/1 ratio)
  4. customsonicated
  5. filtrationThe resulting solid was filtered
  6. washwashed in hexanes
  7. customair dried

Sources & evidence

ORD record
ord-c611f2b032784e43963765761cec4270
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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