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

HRID 2306566ノート

反応式

HRID 2306566 の反応式
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

参加物

4

反応物 2

HCID 12052TriethylsilaneHCID 13330640HCID 13330640、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-63d50dbb78754aba919237c7e01bef4d
出典データセット
uspto-grants-2004_12
特許番号
US06828319B2

反応ノート

読み込み中…