Triethylsilane → HCID 66716896, compound

HRID 1184491Notes

Reaction equation

HRID 1184491 reaction equation
[Br:1][C:2]1[CH:13]=[C:12]([C:14](=O)[CH2:15][CH3:16])[C:5]2[O:6][CH:7]([CH3:11])[C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[CH:13]=[C:12]([CH2:14][CH2:15][CH3:16])[C:5]2[O:6][CH:7]([CH3:11])[C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 66716984HCID 66716984, compound

Product 1

HCID 66716896HCID 66716896, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
40 °C

Procedure

In a 20 mL scintillation vial was added 6-bromo-2-methyl-8-propionyl-2H-benzo[b][1,4]oxazin-3(41)-one 358B (517 mg, 1.734 mmol) and triethylsilane (0.554 mL, 3.47 mmol) in TFA (7.0 mL) and stirred at 40° C. for 4 h. The reaction was concentrated in vacuo and the residue was taken up in EtOAc (25 mL), washed with sat aq NaHCO3 and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified via ISCO flash chromatography (0-100% EtOAc in hexanes; 40 g column). Collected fractions gave the title compound as a yellow solid (249 mg, 0.876 mmol, 50.5% yield). 1H NMR (400 MHz, DMSO-d6): δ=10.69 (s, 1H), 6.98 (d, J=2.5 Hz, 1H), 6.87 (d, J=2.3 Hz, 1H), 4.65 (q, J=6.8 Hz, 1H), 1.48-1.58 (m, 2H), 1.38 (d, J=6.8 Hz, 5H), 0.87 ppm (t, J=7.3 Hz, 3H). ESI-MS: m/z 284.1 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. washwashed with sat aq NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via ISCO flash chromatography (0-100% EtOAc in hexanes; 40 g column)

Sources & evidence

ORD record
ord-f7dfb92602094df380dd8fb37b90435a
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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