Sodium Carbonate → HCID 57754506, compound

HRID 226959Notes

Reaction equation

HRID 226959 reaction equation
Br[C:2]1[N:7]=[C:6]([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[C:11]([C:20](=[O:29])[C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([CH3:28])[CH:22]=3)=[CH:10]2)[CH:5]=[CH:4][CH:3]=1.[N:30]1[CH:35]=[C:34](B(O)O)[CH:33]=[N:32][CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCCC1.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].C(#N)C>[CH3:28][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[CH3:27])[C:20]([C:11]1[C:12](=[O:19])[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]([CH2:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([C:34]3[CH:35]=[N:30][CH:31]=[N:32][CH:33]=3)[N:7]=2)[CH:10]=1)=[O:29]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 16731006HCID 16731006, compound

Product 1

HCID 57754506HCID 57754506, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

90 mg (0.2 mmol) of 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethyl-benzoyl)-1H-quinolin-4-one 4 mm, 50 mg (0.40 mmol) of pyrimidin-5-boronic acid, 18.3 mg (0.02 mmol) of Pd2(dba)3, 21 mg (0.08 mmol) of triphenylphosphine were dissolved in 2 mL of tetrahydrofuran. To the resultant solution was added 0.5 mL (1.0 mmol) of 2N Na2CO3 aqueous solution and the mixture was stirred at 75° C. for 18 h. The reaction mixture was quenched by pouring into a container having 20 mL of water. The crude product precipitated out of solution and was isolated by filtration. The crude product 4oo was purified by flash chromatography to yield 14 mg of colorless a solid: LC-MSD, m/z for C28H22N4O2, [M+H]+=447.5, [M+2H]+=448.5; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.055 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.35 (d, 6H), 5.56 (s, 2H), 7.17 (d, 1H), 7.36-7.48 (m, 2H), 7.52-7.66 (m, 3H), 7.72 (d, 1H), 7.81 (t, 1H), 8.37 (s, 1H), 8.42-8.50 (m, 1H), 9.22-9.32 (m, 3H).

Workup

  1. customThe reaction mixture was quenched
  2. additionby pouring into a container
  3. customThe crude product precipitated out of solution
  4. customwas isolated by filtration
  5. customwas purified by flash chromatography
  6. customto yield 14 mg of colorless a solid

Sources & evidence

ORD record
ord-4b508d9a9b26464c8845365c76ec09bc
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

Loading…