Acetic Acid → 2,3-dihydro-1H-[2,3']bipyridinyl-4-one

HRID 1691833Notes

Reaction equation

HRID 1691833 reaction equation
C[Si](C)(C)CCS([N:8]1[CH:13]=[CH:12][C:11](=[O:14])[CH2:10][CH:9]1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)(=O)=O.[F-].[Cs+].C(O)(=O)C>CN(C=O)C.C(OCC)(=O)C>[NH:8]1[CH:13]=[CH:12][C:11](=[O:14])[CH2:10][CH:9]1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 25953Cesium fluorideHCID 593777611-(2-trimethylsilyl-ethanesulfonyl)-2,3-dihydro-1H-[2,3']bipyridinyl-4-one

Product 1

HCID 593777842,3-dihydro-1H-[2,3']bipyridinyl-4-oneYield 94.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-(2-trimethylsilyl-ethanesulfonyl)-2,3-dihydro-1H-[2,3′]bipyridinyl-4-one (106.1 mg, 0.31 mmol) in DMF (0.5 mL) was added cesium fluoride (153.5 mg, 1.0 mmol) under Ar atmosphere. The mixture was heated at 90° C. for 2 hours, then cooled to room temperature. Acetic acid (0.062 mL, 1.085 mmol) was added, and the mixture was diluted with ethyl acetate and filtered. The filtrate was taken to dryness under reduced pressure. Purification of the residue by flash chromatography (dichloromethane/methanol 95:5) gave 2,3-dihydro-1H-[2,3′]bipyridinyl-4-one (51 mg, 93.5%).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customPurification of the residue by flash chromatography (dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-3ddaee935dfd46e299da634954db6b4a
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

Loading…