Benzyl Bromide → 9-Benzyl-6-fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one

HRID 1057628

반응식

HRID 1057628 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH2:7][C:6](=[O:15])[C:5]2=1.CCCCC.[H-].[Na+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH2:23]([N:11]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:15])[C:5]=2[C:4]2[C:12]1=[CH:13][CH:14]=[C:2]([F:1])[CH:3]=2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

참가 물질

6

반응물 4

HCID 7498Benzyl BromideHCID 8003PentaneHCID 24758Sodium hydrideHCID 3357046-fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one

생성물 1

HCID 186716779-Benzyl-6-fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one수율 66%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6-Fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one (0.3938 g, 0.0019 mol) is added to a slurry of pentane-washed NaH (0.0970 g, 0.0024 mol) in DMF (3 mL) and after stirring for 10 min, benzyl bromide (0.28 mL, 0.0024 mol) is added. After stirring for 4 h at room temperature, the mixture is partitioned between water and ethyl acetate. The combined organic layers are dried over sodium sulfate and concentrated to dryness. The resulting solids are chromatographed on silica gel (200 mL) using dichloromethane/heptane (60/40 to 80/20 to 100/0) to give 0.3681 g (65%) of the title compound. An aliquot is recrystallized from ethyl acetate/heptane; MS (ESI+) for C19H16FNO m/z 294.2 (M+H)+; IR (drift) 1634, 1523, 1483, 1466, 1447, 1357, 1254, 1138, 900, 868, 803, 799, 759, 729, 700 cm−1; 1H NMR (CDCl3) δ2.22, 2.59, 2.88, 5.32, 6.95, 7.01, 7.15, 7.30, 7.96. Anal. Calcd for C19H16FNO: C, 77.80; H, 5.50; N, 4.78. Found: C, 77.65; H, 5.39; N, 4.69.

후처리

  1. stirringAfter stirring for 4 h at room temperature
  2. customthe mixture is partitioned between water and ethyl acetate
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customThe resulting solids are chromatographed on silica gel (200 mL)

출처 및 근거

ORD 기록
ord-c446ea19570a47c58cf2a976012a60af
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514968B1

연결된 노트

불러오는 중…