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Cesium carbonate → HCID 68900138、化合物

HRID 735374
ノート
印刷プレビュー

反応式

HRID 735374 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 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、化合物

生成物 2

HCID 21882781Isohexane ethyl acetate収率 40%HCID 68900138
HCID 68900138、化合物
収率 484%

試薬・触媒・溶媒 4

HCID 70681Tetrabutylammonium Chloride触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

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+].

後処理

  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

出典と根拠

ORDレコード
ord-38ab949f9b6b4467ac4f28b69b2d4ba4
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07592456B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート