Cesium carbonate → HCID 178479984, compound

HRID 1774629Notes

Reaction equation

HRID 1774629 reaction equation
Br[C:2]1[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=[C:6]([Br:8])[CH:7]=1.[NH2:11][C:12]1[N:17]=[C:16]([OH:18])[CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[Br:8][C:6]1[CH:7]=[C:2]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([OH:18])[N:17]=2)[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 1785076342-Amino-6-hydroxypyridine

Product 1

HCID 178479984HCID 178479984, compoundYield 135.1%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3,5-dibromo-1-methylpyridin-2(1H)-one (2.67 g, 10.0 mmol), 6-aminopyridin-2-ol (1.1 g, 10.0 mmol), Pd2(dba)3 (460 mg, 0.5 mmol), Xantphos (576 mg, 1.0 mmol) and Cs2CO3 (6.52 g, 20.0 mmol) in DMF (40 mL) was stirred at 100° C. overnight. The mixture was concentrated and the residue was treated with DCM. The precipitate was collected by filtration and dried to give 5-bromo-3-(6-hydroxypyridin-2-ylamino)-1-methylpyridin-2(1H)-one 101a (4.0 g crude) as a brown solid.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was treated with DCM
  3. filtrationThe precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-10506374d4314852b7ebe43c9d267698
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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