Sodium Methoxide → 4-(1,5-Naphthyridin-4-ylthio)benzenamine

HRID 1042802Notes

Reaction equation

HRID 1042802 reaction equation
C[O-].[Na+].Br[C:5]1[CH:14]=[C:13]2[C:8]([C:9]([S:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)=[CH:10][CH:11]=[N:12]2)=[N:7][CH:6]=1>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:12]1[C:13]2[C:8](=[N:7][CH:6]=[CH:5][CH:14]=2)[C:9]([S:15][C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 673180344-(7-Bromo-1,5-naphthyridin-4-ylthio)benzenamine

Product 1

HCID 594273014-(1,5-Naphthyridin-4-ylthio)benzenamine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of tetrakis(triphenylphosphine)palladium (188 mg, 163 μmol) and sodium methoxide (176 mg, 3251 μmol) was added a solution of 4-(7-bromo-1,5-naphthyridin-4-ylthio)benzenamine (540 mg, 1625 μmol) in DMF (2 mL). The resealable tube was purged with argon, and the mixture was heated to 100° for 1.5 h. The mix was diluted with ethyl acetate, washed with brine twice, dried with sodium sulfate, and concentrated. The residue was purified by silica gel chromatography using 1-10% MeOH:CH2Cl2 w/1% NH4OH to provide 4-(1,5-naphthyridin-4-ylthio)benzenamine. MS m/z=254 [M]+. Calc'd for C14H11N3S: 253.32.

Workup

  1. customThe resealable tube was purged with argon
  2. temperaturethe mixture was heated to 100° for 1.5 h
  3. additionThe mix was diluted with ethyl acetate
  4. washwashed with brine twice
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-cab75656b21a4e6786e4a48f67bef49c
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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