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Cesium carbonate → 4'-Fluoro-1'-{[3-(trifluoromethyl)pyridin-2-yl]methyl}-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'h)-one

HRID 1407725
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HRID 1407725 반응식
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]1([C:23]3[C:14](=[CH:15][C:16]4[O:21][CH2:20][CH2:19][O:18][C:17]=4[CH:22]=3)[O:13][CH2:12]1)[C:5](=[O:11])[NH:6]2.Cl.Cl[CH2:26][C:27]1[C:32]([C:33]([F:36])([F:35])[F:34])=[CH:31][CH:30]=[CH:29][N:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]1([C:23]3[C:14](=[CH:15][C:16]4[O:21][CH2:20][CH2:19][O:18][C:17]=4[CH:22]=3)[O:13][CH2:12]1)[C:5](=[O:11])[N:6]2[CH2:26][C:27]1[C:32]([C:33]([F:35])([F:34])[F:36])=[CH:31][CH:30]=[CH:29][N:28]=1
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참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 593524954'-fluoro-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'H)-oneHCID 667065662-(Chloromethyl)-3-(trifluoromethyl)pyridine hydrochloride

생성물 1

HCID 593525774'-Fluoro-1'-{[3-(trifluoromethyl)pyridin-2-yl]methyl}-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'h)-one수율 82.6%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
60 °C

실험 절차

A mixture of 4′-fluoro-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (0.31 g, 1.00 mmol), 2-(chloromethyl)-3-(trifluoromethyl)pyridine hydrochloride (0.29 g, 1.50 mmol) and cesium carbonate (0.98 g, 3.00 mmol) in N,N′ dimethylformamide (10 mL) was heated at 60° C. for 2 h and was filtered while hot. The filtrate was allowed to cool to ambient temperature and water was added, causing a precipitate to be deposited. The solid was collected by filtration, washed with water (50 mL) and dried under vacuum. The residue was recrystallized from N,N′ dimethylformamide/water to afford 4′-fluoro-1′-{[3-(trifluoromethyl)pyridin-2-yl]methyl}-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (0.39 g, 82%) as a beige solid: mp 245-247° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.68 (d, J=4.5 Hz, 1H), 8.27 (d, J=7.65 Hz, 1H), 7.59 (dd, J=7.8, 4.9 Hz, 1H), 7.30 (ddd, J=8.2, 8.2, 5.8 Hz, 1H), 6.86 (d, J=9.0 Hz, 1H), 6.82 (d, J=7.8 Hz, 1H), 6.54 (s, 1H), 6.49 (s, 1H), 5.25 (ABq, J=17.4 Hz, 2H), 4.79 (q, J=9.4 Hz, 2H), 4.22-4.10 (m, 4H); 13C NMR (75 MHz, DMSO-d6) δ 176.5, 157.9 (d, 1JC-F=247 Hz), 154.6, 152.3, 152.1 (d, 5JC-F=1.2 Hz), 144.9 (d, 4JC-F=8.9 Hz), 144.3, 137.6, 135.1 (q, 4JC-F=4.9 Hz), 130.8 (d, 4JC-F=8.6 Hz), 125.6 (q, 1JC-F=274 Hz), 123.0, 122.9 (d, 2JC-F=32.3 Hz), 119.4, 117.1 (d, 3JC-F=19.3 Hz), 111.5, 109.9 (d, 3JC-F=19.9 Hz), 105.7 (d, 5JC-F=2.9 Hz), 98.4, 77.4, 64.1, 63.5, 56.0 (d, 5JC-F=1.7 Hz), 42.3 (q, 5JC-F=3.3 Hz); MS (ES+) m/z 460.9 (M+1).

후처리

  1. filtrationwas filtered while hot
  2. temperatureto cool to ambient temperature
  3. additionwater was added
  4. filtrationThe solid was collected by filtration
  5. washwashed with water (50 mL)
  6. customdried under vacuum
  7. customThe residue was recrystallized from N,N′ dimethylformamide/water

출처 및 근거

ORD 기록
ord-442233ce14cb41208fd12353060c43b2
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08916580B2

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