Sodium Carbonate → HCID 11957743, compound

HRID 1446103Notes

Reaction equation

HRID 1446103 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.C([O-])([O-])=O.[Na+].[Na+].Br[C:17]1[CH:26]=[CH:25][C:24]2[N:23]=[CH:22][C:21]3[N:27]([CH3:42])[C:28](=[O:41])[N:29]([C:30]4[CH:35]=[CH:34][C:33]([C:36]([CH3:40])([CH3:39])[C:37]#[N:38])=[CH:32][CH:31]=4)[C:20]=3[C:19]=2[CH:18]=1>CN(C=O)C.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:39][C:36]([C:33]1[CH:32]=[CH:31][C:30]([N:29]2[C:20]3[C:19]4[CH:18]=[C:17]([C:4]5[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=5)[CH:26]=[CH:25][C:24]=4[N:23]=[CH:22][C:21]=3[N:27]([CH3:42])[C:28]2=[O:41])=[CH:35][CH:34]=1)([CH3:40])[C:37]#[N:38]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 426095702-[4-(8-Bromo-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl]-2-methylpropanenitrile

Product 1

HCID 11957743HCID 11957743, compound

Reagents, catalysts & solvents 2

HCID 178419050HCID 178419050, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

37 mg (0.3 mmol) of 4-pyridineboronic acid (Aldrich, Buchs, Switzerland), 8 mg of bis(triphenylphosphine)palladium (II) dichloride (Fluka, Buchs, Switzerland) and 0.5 ml of a 1 M solution of Na2CO3 are added to a solution of 84 mg (0.2 mmol) of 2-[4-(8-bromo-3-methyl-2-oxo-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-phenyl]-2-methyl-propionitrile (Example 1i) in 2 ml of DMF. The mixture is stirred for 1 h at 100° C. After this time, the mixture is quenched with sat. aqueous NaHCO3 and extracted with EtOAc (2×). The organic layer is washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. The residue is loaded on silica gel and purified by flash chromatography (CH2Cl2-MeOH 97:3 to 18:1) to give the title compound as an off-white solid. ES-MS: 420 (M+H)+; analytical HPLC: tret=2.40 min (Grad 1).

Workup

  1. customAfter this time, the mixture is quenched with sat. aqueous NaHCO3
  2. extractionextracted with EtOAc (2×)
  3. washThe organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. custompurified by flash chromatography (CH2Cl2-MeOH 97:3 to 18:1)

Sources & evidence

ORD record
ord-c17966ad53444a5896114025be30cd8f
Source dataset
uspto-grants-2010_02
Patent number
US07667039B2

Reaction notes

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