Potassium Carbonate → Tert-butyl 3-(3-methylpyridin-4-yl)benzoate

HRID 338570

반응식

HRID 338570 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH3:8].[C:9]([O:13][C:14]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>COCCOC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:8][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[C:20]1[CH:21]=[C:16]([CH:17]=[CH:18][CH:19]=1)[C:14]([O:13][C:9]([CH3:11])([CH3:12])[CH3:10])=[O:15]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 27577094-Chloro-3-methylpyridineHCID 2773299(3-((Tert-butoxy)carbonyl)phenyl)boronic acid

생성물 1

HCID 57895121Tert-butyl 3-(3-methylpyridin-4-yl)benzoate수율 71.4%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
80 °C

실험 절차

4-Chloro-3-methylpyridine (2.00 g, 15.7 mmol), 3-(tert-butoxycarbonyl)phenylboronic acid (5.42 g, 24.4 mmol), a 2M aqueous solution of potassium carbonate (31.4 mL, 62.8 mmol), and palladium tetrakis(triphenylphosphine) (Pd(PPh3)4, 0.906 g, 0.784 mmol) were suspended in 1,2-dimethoxyethane (DME, 150 mL). The resulting mixture was stirred and heated to 80° C. for 60 hours. The crude reaction mixture was cooled to room temperature and then the layers were separated. The organic layer was evaporated to dryness and then purified on 120 g of silica gel utilizing a gradient of 0-70% ethyl acetate in hexanes to yield the pure product as a pale yellow oil (3.02 g, 11.2 mmol, 71.4%).

후처리

  1. customThe crude reaction mixture
  2. temperaturewas cooled to room temperature
  3. customthe layers were separated
  4. customThe organic layer was evaporated to dryness
  5. custompurified on 120 g of silica gel utilizing a gradient of 0-70% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-ad087937869e45669e753b6ee4cfb5c9
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889875B2

연결된 노트

불러오는 중…