Potassium Carbonate → HCID 69461972, compound

HRID 2376630Notes

Reaction equation

HRID 2376630 reaction equation
Br[C:2]1[N:3]=[C:4]([NH2:12])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C([O-])([O-])=O.[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:38][C:39]1[CH:40]=[CH:41][C:42]([O:48][CH3:49])=[C:43](B(O)O)[CH:44]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.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].CN(C=O)C>[F:38][C:39]1[CH:44]=[CH:43][C:42]([O:48][CH3:49])=[C:41]([C:2]2[N:3]=[C:4]([NH2:12])[CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)[CH:40]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 107043358-Bromo-1,7-naphthyridin-6-amine

Product 1

HCID 69461972HCID 69461972, compound

Reagents, catalysts & solvents 4

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 8-bromo-[1,7]naphthyridin-6-ylamine (1.70 g) in a mixture of toluene (7 ml), DMF (11 ml) and aqueous K2CO3 (2.31 g in 5 ml water) is added bis(dibenzylideneacetone)palladium (174 mg), triphenylphosphine (158 mg) and 5-fluoro-2-methoxyphenylboronic acid (1.38 g). The mixture is stirred for 3.5 hours at 100° C., then diluted with ethyl acetate and filtered through Celite. The ethyl acetate solution is washed with 2N NaOH and water, dried over magnesium sulphate, then concentrated to afford the title compound. MS: APCI 270.0 MH+.

Workup

  1. filtrationfiltered through Celite
  2. washThe ethyl acetate solution is washed with 2N NaOH and water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1dd204252bcb41c09d9f43e23480c1fa
Source dataset
uspto-grants-2008_12
Patent number
US07468370B2

Reaction notes

Loading…