Pentane → 6-Fluoro-9-(4-fluorobenzyl)-1,2,3,9-tetrahydro-4H-carbazol-4-one

HRID 1057631

반응식

HRID 1057631 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+].[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:28][C:27]1[CH:30]=[CH:31][C:24]([F:23])=[CH:25][CH:26]=1)[C:10]1[CH2:9][CH2:8][CH2:7][C:6](=[O:15])[C:5]2=1

참가 물질

6

반응물 4

HCID 8003PentaneHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 3357046-fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one

생성물 1

HCID 186716586-Fluoro-9-(4-fluorobenzyl)-1,2,3,9-tetrahydro-4H-carbazol-4-one수율 96%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6-Fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one (0.3940 g, 0.0019 mol) is added to a slurry of pentane-washed NaH (0.0966 g, 0.0024 mol) in DMF (3 mL) and after stirring for 10 min, p-fluorobenzyl bromide (0.29 mL, 0.0023 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 (100 mL) using methanol/dichloromethane (0.5/99.5) to give 0.5678 g (94%) of the title compound. An aliquot is recrystallized from ethyl acetate/heptane; mp 182.5-183° C.; MS (ESI+) for C19H15F2NO m/z 312.2 (M+H)+; IR (drift) 1631, 1511, 1483, 1466, 1449, 1256, 1228, 1218, 1137, 1094, 867, 836, 813, 808, 802 cm−1; 1H NMR (CDCl3) δ2.24, 2.58, 2.86, 5.28, 6.94, 7.13, 7.96. Anal. Calcd for C19H15F2NO: C, 73.30; H, 4.86; N, 4.50. Found: C, 73.27; H, 4.92; N, 4.54.

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 (100 mL)

출처 및 근거

ORD 기록
ord-206bf3446fa84fea9236f201df7a3a90
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514968B1

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