Potassium Carbonate → 5-(3-Acetyl-5-chloro-2-ethoxy-6-methylphenyl)-N,N-dimethylpyridine-2-carboxamide

HRID 1499692Notes

Reaction equation

HRID 1499692 reaction equation
[Cl:1][C:2]1[C:3]([CH3:15])=[C:4](I)[C:5]([O:11][CH2:12][CH3:13])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH3:16][N:17]([CH3:35])[C:18]([C:20]1[CH:25]=[CH:24][C:23](B2OC(C)(C)C(C)(C)O2)=[CH:22][N:21]=1)=[O:19].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:8]([C:6]1[C:5]([O:11][CH2:12][CH3:13])=[C:4]([C:23]2[CH:24]=[CH:25][C:20]([C:18]([N:17]([CH3:35])[CH3:16])=[O:19])=[N:21][CH:22]=2)[C:3]([CH3:15])=[C:2]([Cl:1])[CH:7]=1)(=[O:10])[CH3:9]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 57416491N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamideHCID 866668651-(5-Chloro-2-ethoxy-3-iodo-4-methylphenyl)ethanone

Product 1

HCID 866776375-(3-Acetyl-5-chloro-2-ethoxy-6-methylphenyl)-N,N-dimethylpyridine-2-carboxamideYield 83.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of 1-(5-chloro-2-ethoxy-3-iodo-4-methylphenyl)ethanone (0.69 g, 2.0 mmol) and N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide (0.68 g, 2.4 mmol) in 1,4-dioxane (10 mL), potassium carbonate (0.56 g, 4.1 mmol) in water (3 mL, 200 mmol) was added. The reaction was bubbled with N2. Tetrakis(triphenylphosphine)palladium(0) (0.24 g, 0.20 mmol) was added and N2 was bubbled. Reaction was stirred overnight at 95° C. The reaction was diluted with water, extracted with EtOAc. The combined organic layers were dried over MgSO4, concentrated and purified on silica gel (eluting with 0 to 90% EtOAc in hexanes) to give the desired product (0.6 g, 82%). LCMS calculated for C19H22ClN2O3 (M+H)+: m/z=361.1; Found: 361.0.

Workup

  1. additionwas added
  2. customThe reaction was bubbled with N2
  3. customN2 was bubbled
  4. customReaction
  5. extractionextracted with EtOAc
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated
  8. custompurified on silica gel (eluting with 0 to 90% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2d44455fde684c09b7e5d5db70547296
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

Loading…