Cycloheptanone → 2-(2-Methylpyridin-4-yl)cycloheptanone

HRID 2088720Notes

Reaction equation

HRID 2088720 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.[C:9]1(=[O:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC(O)C.C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:8][C:4]1[CH:3]=[C:2]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:9]2=[O:16])[CH:7]=[CH:6][N:5]=1

Participants

8

Reactant 4

HCID 10400CycloheptanoneHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27628354-Bromo-2-methylpyridine

Product 1

HCID 689234062-(2-Methylpyridin-4-yl)cycloheptanone

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-bromo-2-methylpyridine (300 mg, 1.744 mmol), cycloheptanone (0.206 mL, 1.744 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (121 mg, 0.209 mmol), Pd2(dba)3 (80 mg, 0.087 mmol), and Cs2CO3 (739 mg, 2.267 mmol) in 2-propanol (1.5 mL) and toluene (1.5 mL) was stirred at 85° C. overnight. After this time, the mixture was filtered through diatomaceous earth, then the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica gel (7:3 hexane-EtOAc, eluant) to afford the title compound. MS (APCI+) m/z 204 (M+H)+.

Workup

  1. filtrationAfter this time, the mixture was filtered through diatomaceous earth
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by chromatography on silica gel (7:3 hexane-EtOAc, eluant)

Sources & evidence

ORD record
ord-e77422a1696f465a8758f2d81b9e3696
Source dataset
uspto-grants-2013_05
Patent number
US08436005B2

Reaction notes

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