Potassium Phosphate, Tribasic → HCID 56847586, compound

HRID 1467388Notes

Reaction equation

HRID 1467388 reaction equation
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]

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 108485903-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinolineHCID 86689179HCID 86689179, compound

Product 1

HCID 56847586HCID 56847586, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 977OxygenSolvent

Conditions

Temperature
130 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-9d5759e8150e4e7795fe6eef1466583a
Source dataset
uspto-grants-2015_04
Patent number
US09000153B2

Reaction notes

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