Cesium carbonate → HCID 178479984, compound

HRID 1774620Notes

Reaction equation

HRID 1774620 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[CH:4][CH:3]=1.Br[C:10]1[C:11](=[O:18])[N:12]([CH3:17])[CH:13]=[C:14]([Br:16])[CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].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>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].CN(C=O)C>[Br:16][C:14]1[CH:15]=[C:10]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]([OH:8])[N:7]=2)[C:11](=[O:18])[N:12]([CH3:17])[CH:13]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 1785076342-Amino-6-hydroxypyridine

Product 1

HCID 178479984HCID 178479984, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A 100 mL round-bottomed flask equipped with a reflux condenser was charged with 6-aminopyridin-2-ol (1.1 g, 10.0 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (2.67 g, 10.0 mmol), cesium carbonate (6.52 g, 20.0 mmol), xantphos (576 mg, 1.0 mmol), Pd2(dba)3 (460 mg, 0.50 mmol), and DMF (35 mL). The system was subject to three cycles of vacuum/argon flush and heated at 100° C. for 3 h. It was then cooled to room temperature and filtered. The filtrate was diluted with DCM (500 mL) and washed with H2O (80 mL×3). The organic layer was dried and concentrated under reduced pressure. The residue solid was purified by silica-gel column-chromatography eluting with DCM/MeOH (30:1 to 15:1) to afford 101a (580 mg, 20%) as yellow solid. MS-ESI: [M+H]+ 296.0

Workup

  1. customA 100 mL round-bottomed flask equipped with a reflux condenser
  2. customflush
  3. temperatureIt was then cooled to room temperature
  4. filtrationfiltered
  5. additionThe filtrate was diluted with DCM (500 mL)
  6. washwashed with H2O (80 mL×3)
  7. customThe organic layer was dried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue solid was purified by silica-gel column-chromatography
  10. washeluting with DCM/MeOH (30:1 to 15:1)

Sources & evidence

ORD record
ord-ba545948223b408782a738b6b3c43d1b
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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