Trifluoroacetic acid → HCID 135410954, compound

HRID 853665Notes

Reaction equation

HRID 853665 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[CH:27]([OH:39])[N:28]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[C:29](=O)[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:36]=[CH:37][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])[CH2:29]2)=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58928932HCID 58928932, compound

Product 1

HCID 135410954HCID 135410954, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a flask containing 5-benzhydryloxy-7-(4-fluoro-benzyl)-8-hydroxy-9-methoxy-7,8-dihydro-pyrrolo[3,4-g]quinoxalin-6-one 247a (20 mg, 0.038 mmol, 1 equiv.) was added CH2Cl2 (1 mL) under a nitrogen atmosphere. Triethylsilane (200 μL) was added followed by trifluoroacetic acid (200 μL). The reaction was allowed to stir for 1 hour and then concentrated in vacuo until thoroughly dried. To the oil was Hexanes/Ethyl ether (15 mL, 1/1 ratio) and sonicated. The resulting solid was then filtered, washed in hexanes, and air dried to give 7-(4-fluoro-benzyl)-5-hydroxy-9-methoxy-7,8-dihydro-pyrrolo[3,4-g]quinoxalin-6-one 248 (38%, 7.2 mg, 0.0.14 mmol). 1H NMR (300 MHz) CDCl3 δ 8.95 (d, J=13.8 Hz, 2 H), 7.23-7.27 (m, 2 H), 6.96-7.05 (s, 2 H), 4.79 (2 H), 4.55 (s, 2 H), 4.14 (s, 3 H). 19F NMR (300 MHz) CDCl3 δ 62.80. MS: 340.1 (M+1)

Workup

  1. concentrationconcentrated in vacuo
  2. customuntil thoroughly dried
  3. customsonicated
  4. filtrationThe resulting solid was then filtered
  5. washwashed in hexanes
  6. customair dried

Sources & evidence

ORD record
ord-196989b140df4369bd17024beb750497
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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