Ethyl Acetate → 5-(2-Ethyl-5-methylsulfonylphenyl)-1-methylpyridin-2-one

HRID 518508Notes

Reaction equation

HRID 518508 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH3:12])(=[O:11])=[O:10])=[CH:5][C:4]=1I)[CH3:2].[CH3:14][N:15]1[CH:20]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH:18]=[CH:17][C:16]1=[O:30].C([O-])([O-])=O.[K+].[K+].CC(=O)OCC>O1CCOCC1.O.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]>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH3:12])(=[O:11])=[O:10])=[CH:5][C:4]=1[C:19]1[CH:18]=[CH:17][C:16](=[O:30])[N:15]([CH3:14])[CH:20]=1)[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 454801941-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-oneHCID 585218301-Ethyl-2-iodo-4-(methylsulfonyl)benzene

Product 1

HCID 1180215995-(2-Ethyl-5-methylsulfonylphenyl)-1-methylpyridin-2-oneYield 97.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

The title compound of step 3 (62 mg, 0.2 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (57 mg, 0.24 mmol), K2CO3 (82 mg, 0.6 mmol), Pd(dppf)Cl2 (6.2 mg) in 1,4-dioxane/water (4:1) (5 mL) were heated at 85° C. under N2 overnight. Silica gel chromatography (PE:EA=1:1) gave the title compound (56.6 mg, 97%) as a brown oil. 1H NMR (300 MHz, CDCl3): δ 1.66 (3H, t, J=6.0 Hz), 2.63-2.71 (2H, m), 3.05 (3H, s), 3.60 (3H, s), 6.64 (1H, d, J=9.0 Hz), 7.28-7.33 (2H, m), 7.48 (1H, d, J=9.0 Hz), 7.70 (1H, s), 7.82-7.85 (1H, m). LCMS: 292 (M+1)+

Sources & evidence

ORD record
ord-8a6a8404c8e748d58a2c1c0216941602
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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