Potassium Carbonate → HCID 68868568, compound

HRID 2376628Notes

Reaction equation

HRID 2376628 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10](Br)[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]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]=[C:41](B(O)O)[CH:42]=[CH:43][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]=[C:43]([C:10]2[N:11]=[C:2]([NH2:1])[CH:3]=[C:4]3[C:9]=2[N:8]=[CH:7][CH:6]=[CH:5]3)[CH:42]=[CH:41][CH:40]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27339863-Fluorophenylboronic acidHCID 107043358-Bromo-1,7-naphthyridin-6-amine

Product 1

HCID 68868568HCID 68868568, 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 6-amino-8-bromo-1,7-naphthyridine (0.5 g) in a mixture of toluene (2.5 ml), DMF (4 ml) and aqueous K2CO3 (0.68 g in 2 ml water) is added bis(dibenzylideneacetone)palladium (51 mg), triphenylphosphine (47 mg) and 3-fluorphenylboronic acid (0.33 g). The mixture is stirred for 4 hours at 100° C. The mixture is diluted with ethyl acetate, then filtered through a Celite™ filter. The ethyl acetate solution is washed with 2 N NaOH and water, dried over magnesium sulphate, then concentrated to afford the title compound. MS: APCI 240.0 MH+.

Workup

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

Sources & evidence

ORD record
ord-1b6b28c25dde457cbbe374a323f649e8
Source dataset
uspto-grants-2008_12
Patent number
US07468370B2

Reaction notes

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