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Potassium Phosphate, Tribasic → 3-fluoro-4-{7-methoxy-3-methyl-2-oxo-8-[(E)-2-thiophen-3-ylvinyl]-2,3-dihydroimidazo[4,5-c]quinolin-1-yl}benzonitrile

HRID 1467387
ノート
印刷プレビュー

反応式

HRID 1467387 の反応式
FC(F)(F)S(O[C:7]1[C:16]([O:17][CH3:18])=[CH:15][C:14]2[N:13]=[CH:12][C:11]3[N:19]([CH3:32])[C:20](=[O:31])[N:21]([C:22]4[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][C:23]=4[F:30])[C:10]=3[C:9]=2[CH:8]=1)(=O)=O.CC1(C)C(C)(C)OB(/[CH:43]=[CH:44]/[C:45]2[CH:49]=[CH:48][S:47][CH:46]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O=O>[F:30][C:23]1[CH:24]=[C:25]([CH:26]=[CH:27][C:22]=1[N:21]1[C:10]2[C:9]3[CH:8]=[C:7](/[CH:43]=[CH:44]/[C:45]4[CH:49]=[CH:48][S:47][CH:46]=4)[C:16]([O:17][CH3:18])=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:19]([CH3:32])[C:20]1=[O:31])[C:28]#[N:29]
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

5

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 162183494,4,5,5-Tetramethyl-2-[(E)-2-(thiophen-3-yl)ethenyl]-1,3,2-dioxaborolaneHCID 866891791-(4-Cyano-2-fluorophenyl)-7-methoxy-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl trifluoromethanesulfonate

生成物 1

HCID 568476433-fluoro-4-{7-methoxy-3-methyl-2-oxo-8-[(E)-2-thiophen-3-ylvinyl]-2,3-dihydroimidazo[4,5-c]quinolin-1-yl}benzonitrile収率 75.4%

試薬・触媒・溶媒 1

HCID 977Oxygen溶媒

反応条件

温度
130 °C

実験手順

1-(4-Cyano-2-fluorophenyl)-7-methoxy-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl trifluoromethanesulfonate (119 mg, 240 μmol), 4,4,5,5-tetramethyl-2-[(E)-2-thiophen-3-ylvinyl]-1,3,2-dioxaborolane (142 mg, 602 μmol), tripotassium phosphate (107 mg, 504 μmol) and trans-bis(tricyclohexylphosphine)palladium(II) dichloride (18 mg, 24 μmol) were dissolved in oxygen-free N,N-dimethylformamide (5 ml). The mixture was subsequently heated at 130° C. for 45 min (microwave). The reaction mixture was then filtered with suction, the filtrate was diluted with water and stirred at room temperature for 30 min. The precipitate formed was filtered off with suction and rinsed with water. The residue was chromatographed on flash silica gel (solvent gradient ethyl acetate/0-25% by vol. of ethanol), giving 3-fluoro-4-{7-methoxy-3-methyl-2-oxo-8-[(E)-2-thiophen-3-ylvinyl]-2,3-dihydroimidazo[4,5-c]quinolin-1-yl}benzonitrile (90 mg, 181 μmol) as solid. MS: 457.1 (M+H+), TLC (HPTLC): Rf=0.47 (ethyl acetate/ethanol 2:1, parts by volume).

後処理

  1. filtrationThe reaction mixture was then filtered with suction
  2. additionthe filtrate was diluted with water
  3. customThe precipitate formed
  4. filtrationwas filtered off with suction
  5. washrinsed with water
  6. customThe residue was chromatographed on flash silica gel (solvent gradient ethyl acetate/0-25% by vol. of ethanol)

出典と根拠

ORDレコード
ord-048283d548bf4cf7954bf1730f8d78bd
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09000153B2

反応ノート

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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