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Cesium carbonate → HCID 68900138, 화합물

HRID 735374
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HRID 735374 반응식
FC(F)(F)S([O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[C:24]#[N:25])[CH:13]=2)[CH:8]=1)(=O)=O.[C:28]1([S:34]([O-:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2[C:64]3[O:63][C:62]4C(=CC=C[C:61]=4P(C4C=CC=CC=4)C4C=CC=CC=4)[C:56](C)(C)[C:55]=3[CH:54]=[CH:53][CH:52]=2)C=CC=CC=1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[C:62]([O:6][CH2:7][CH3:16])(=[O:63])[CH3:61].[CH3:52][CH2:53][CH2:54][CH:55]([CH3:56])[CH3:64].[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:12]2[CH:11]=[CH:10][C:9]3[C:14](=[CH:15][CH:16]=[C:7]([S:34]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)(=[O:36])=[O:35])[CH:8]=3)[CH:13]=2)=[C:18]([CH:19]=1)[C:24]#[N:25]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 2723840Benzenesulfinic acid, sodium saltHCID 86616739HCID 86616739, 화합물

생성물 2

HCID 21882781Isohexane ethyl acetate수율 40%HCID 68900138
HCID 68900138, 화합물
수율 484%

시약·촉매·용매 4

HCID 70681Tetrabutylammonium Chloride촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
120 °C

실험 절차

A mixture of 6-(2-cyano-4-fluorophenyl)-2-naphthyl trifluoromethanesulfonate (0.65 g, 1.65 mmol), sodium benzene sulfinate (0.33 g, 1.97 mmol), cesium carbonate (0.81 g, 2.48 mmol), tris(dibenzylideneacetone)dipalladium(0) (38 mg, 0.04 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (49 mg, 0.08 mmol) and tetrabutylammonium chloride (0.55 g, 1.98 mmol) in toluene (15 mL) was heated at 120° C. under nitrogen for 4 hours. It was allowed to cool, poured into water (150 mL) and extracted with ethyl acetate (2×100 mL). These extracts were washed with water and brine then dried (MgSO4), filtered and solvent removed in vacuo. Purification by flash column chromatography eluting with 20% ethyl acetate/isohexane then 40% ethyl acetate/isohexane gave 5-fluoro-2-[6-(phenylsulfonyl)-2-naphthyl]benzonitrile (150 mg, 23%). 1H NMR (500 MHz, d6-DMSO) δ 8.82 (1H, s), 8.38 (1H, d, J=8.5 Hz), 8.26 (1H, s), 8.23 (1H, d, J=8.7 Hz), 8.05-8.03 (3H, m), 7.98 (1H, d, J=8.6 Hz), 7.88 (1H, d, J=8.5 Hz), 7.81-7.63 (5H, m); m/z (ES+) 388 [MH+].

후처리

  1. temperatureto cool
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThese extracts were washed with water and brine
  4. dry with materialthen dried (MgSO4)
  5. filtrationfiltered
  6. customsolvent removed in vacuo
  7. customPurification by flash column chromatography
  8. washeluting with 20% ethyl acetate/isohexane

출처 및 근거

ORD 기록
ord-38ab949f9b6b4467ac4f28b69b2d4ba4
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07592456B2

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