Sodium Carbonate → HCID 59436011, compound

HRID 1802479Notes

Reaction equation

HRID 1802479 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]=[C:7]([NH:16][C:17]3[C:22]([Cl:23])=[CH:21][C:20](I)=[CH:19][C:18]=3[Cl:25])[C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12]([O:14][CH3:15])[N:11]=[CH:10][CH:9]=3.[NH:28]1[C:32](B(O)O)=[CH:31][CH:30]=[N:29]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C.C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Br:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]=[C:7]([NH:16][C:17]3[C:22]([Cl:23])=[CH:21][C:20]([C:30]4[NH:29][N:28]=[CH:32][CH:31]=4)=[CH:19][C:18]=3[Cl:25])[C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12]([O:14][CH3:15])[N:11]=[CH:10][CH:9]=3

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 112519791H-Pyrazole-5-boronic acidHCID 59435979HCID 59435979, compound

Product 1

HCID 59436011HCID 59436011, compound

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 6228DimethylformamideSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 9-bromo-N-(2,6-dichloro-4-iodophenyl)-1-methoxybenzo[c]-2,6-naphthyridin-5-amine (500 mg, 0.87 mmol) in DMF (20 mL), was added 1H-pyrazol-5-ylboronic acid (107 mg, 0.96 mmol), PdCl2(dppf)-CH2Cl2 adduct (142 mg, 0.17 mmol) and sodium carbonate (0.87 mL, 1.74 mmol, 2M in water). The solution was heated to 100° C. in the microwave in a sealed tube for 45 min. The reaction was diluted with ethyl acetate:THF (2:1) and extracted with water followed by brine. The organic layer was dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with THF in hexanes(10-50%) to afford the title compound.

Workup

  1. extractionextracted with water
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel eluting with THF in hexanes(10-50%)

Sources & evidence

ORD record
ord-29ccf65ea4324b07a315cc2c8264d1a0
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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