Triethylsilane → 5,6-dihydro-5-oxo-11H-indeno [1,2-c]isoquinoline

HRID 2306566Notes

Reaction equation

HRID 2306566 reaction equation
O[CH:2]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:19])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[O:19]=[C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH2:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=3[C:9]=2[NH:10]1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 13330640HCID 13330640, compound

Product 1

HCID 101053885,6-dihydro-5-oxo-11H-indeno [1,2-c]isoquinolineYield 87.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred solution of the alcohol 3a (0.35 g, 1.4 mmol) in trifluoroacetic acid (10 mL) was added at room temperature triethylsilane (0.812 g, 7 mmol) and the reaction mixture was stirred for 24 h. Trifluoroacetic acid was evaporated in vacuo and EtOAc was added to the resulting crude product. The resulting solid was filtered and washed with H2O and EtOAc to provide the above-titled compound 6 (0.285 g, 87%). 1H NMR (DMSO-D6): δ 3.89 (s, 2H), 7.30-7.47 (m, 3H), 7.59 (d, J=6.9 Hz, 1H), 7.72-7.74 (m, 2H), 7.98 (d, J=7.8 Hz, 1H), 8.23 (d, J=8.4 Hz, 1H), 12.31 (s, 1H); 13C NMR(DMSO-D6): δ 33.51, 116.50, 120.19, 124.01, 125.51, 125.55, 126.42, 127.50, 127.68, 128.56, 133.45, 136.39, 137.53, 140.18, 143.80, 163.46; MS (ES−): m/z 232.1 (M−1); Anal. Calcd for C16H11NO: C, 82.38; H, 4.75; N, 6.00. Found: C, 81.79; H, 4.45, N, 5.99.

Workup

  1. customTrifluoroacetic acid was evaporated in vacuo and EtOAc
  2. additionwas added to the resulting crude product
  3. filtrationThe resulting solid was filtered
  4. washwashed with H2O and EtOAc

Sources & evidence

ORD record
ord-63d50dbb78754aba919237c7e01bef4d
Source dataset
uspto-grants-2004_12
Patent number
US06828319B2

Reaction notes

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