Cesium carbonate → HCID 178442384, compound

HRID 533935Notes

Reaction equation

HRID 533935 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5](O)=[CH:4][CH:3]=1.[CH3:9][CH:10]([CH3:14])[CH2:11][C:12]#[CH:13].C(=O)([O-])[O-:16].[Cs+].[Cs+]>[Cu]I.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].CN(C=O)C>[CH3:9][CH:10]([CH3:14])[CH2:11][C:12]#[C:13][C:5]1[CH:4]=[CH:3][C:2]([OH:16])=[N:7][CH:6]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 1389484-Methyl-1-pentyneHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 178442384HCID 178442384, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 6-bromo-pyridin-3-ol (1.0 g), 4-methyl-pent-1-yne (872 μL) and DMF (5 mL) under argon was added cesium carbonate (3.28 g), CuI (137 mg) and Pd(dppf)Cl2. The mixture was heated to 80° C. for 4 hours. After reaching room temperature the mixture was filtered and concentrated. The residue was purified by chromatography (silica gel, EA/heptane 1:1 to EA/heptane/MeOH 9:9:2) to provide the subtitle compound. MS ESI+: m/z=176 [M+H]+.

Workup

  1. customAfter reaching room temperature
  2. filtrationwas filtered
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography (silica gel, EA/heptane 1:1 to EA/heptane/MeOH 9:9:2)

Sources & evidence

ORD record
ord-16ccbd0306364e6e830a724ed2be66d5
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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