Potassium Phosphate, Tribasic → 3-Fluoro-4-(7-methoxy-3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydroimidazo[4,5-c]quinolin-1-yl)benzonitrile

HRID 1467388노트

반응식

HRID 1467388 반응식
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([C:43]2[CH:44]=[N:45][C:46]3[C:51]([CH:52]=2)=[CH:50][CH:49]=[CH:48][CH:47]=3)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]([C:43]4[CH:44]=[N:45][C:46]5[C:51]([CH:52]=4)=[CH:50][CH:49]=[CH:48][CH:47]=5)[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]

참가 물질

5

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 108485903-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinolineHCID 866891791-(4-Cyano-2-fluorophenyl)-7-methoxy-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl trifluoromethanesulfonate

생성물 1

HCID 568475863-Fluoro-4-(7-methoxy-3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydroimidazo[4,5-c]quinolin-1-yl)benzonitrile수율 54.1%

시약·촉매·용매 1

HCID 977Oxygen용매

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온도
130 °C

실험 절차

1-(4-Cyano-2-fluorophenyl)-7-methoxy-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl trifluoromethanesulfonate (79 mg, 159 μmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (325 mg, 1.27 mmol), tripotassium phosphate (70 mg, 319 μmol) and trans-bis(tricyclohexylphosphine)palladium(II) dichloride (35 mg, 48 μmol) were dissolved in oxygen-free N,N-dimethylformamide (4.7 ml). The reaction mixture was subsequently heated at 130° C. for 90 min (microwave). The mixture was then decanted off into water (50 ml) and stirred for a further 30 min. The precipitate formed was filtered off with suction and rinsed with water. The filter cake was subsequently suspended in a little cold dimethyl sulfoxide, filtered off and rinsed with 2-propanol, giving 3-fluoro-4-(7-methoxy-3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydroimidazo[4,5-c]quinolin-1-yl)benzonitrile (41 mg, 86 μmol) as colourless solid after drying in a high vacuum. MS: 476.1 (M+H+), TLC (HPTLC): Rf=0.24 (ethyl acetate/ethanol 5:1, parts by volume).

후처리

  1. customThe mixture was then decanted off into water (50 ml)
  2. customThe precipitate formed
  3. filtrationwas filtered off with suction
  4. washrinsed with water
  5. filtrationfiltered off
  6. washrinsed with 2-propanol

출처 및 근거

ORD 기록
ord-9d5759e8150e4e7795fe6eef1466583a
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000153B2

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