Cesium carbonate → HCID 66665859, compound

HRID 221790Notes

Reaction equation

HRID 221790 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[F:11][CH2:12]OS(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[F:11][CH2:12][O:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 13862289Fluoromethyl 4-methylbenzenesulfonateHCID 299497345-Hydroxy-3-methylpyridine-2-carbonitrile

Product 1

HCID 66665859HCID 66665859, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-hydroxy-3-methyl-pyridine-2-carbonitrile (CAS registry 228867-86-5) (228 mg, 1.70 mmol) in DMF (10 ml) was added a solution of toluene-4-sulfonic acid fluoromethyl ester (CAS registry 114435-86-8) (521 mg, 2.55 mmol) and Cs2CO3 (1.386 g, 4.26 mmol) in DMF (4 ml). The reaction mixture was stirred for 1 h at 100° C., then for 1 h at 70° C., diluted with EtOAc and washed with saturated aqueous NH4Cl soln. and brine. The aqueous layers were reextracted with EtOAc, the combined organic layers dried over Na2SO4, filtrated and the filtrate was concentrated. The title compound was obtained as a white solid after flash chromatography on silica gel (cyclohexane/EtOAc gradient 0-3 min 95:5, 3-30 min 95:5 to 65:35).

Workup

  1. waitfor 1 h at 70° C.
  2. washwashed with saturated aqueous NH4Cl soln
  3. dry with materialthe combined organic layers dried over Na2SO4
  4. filtrationfiltrated
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-330211d287134c17b2cf46563e9f6f1d
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

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