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

HRID 2306566노트

반응식

HRID 2306566 반응식
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

참가 물질

4

반응물 2

HCID 12052TriethylsilaneHCID 13330640HCID 13330640, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-63d50dbb78754aba919237c7e01bef4d
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06828319B2

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