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

HRID 1499692노트

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HRID 1499692 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매

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온도
95 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2d44455fde684c09b7e5d5db70547296
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199982B2

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