2-Bromopyridine → 2-(Pyridin-2-YL)benzoic acid

HRID 880261

반응식

HRID 880261 반응식
B([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])(O)O.Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>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]>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

참가 물질

7

반응물 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 27339852-(Dihydroxyboranyl)benzoic acid

생성물 1

HCID 157331752-(Pyridin-2-YL)benzoic acid수율 42.9%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
125 °C

실험 절차

A mixture of 2-boronobenzoic acid (400 mg, 2.4 mmol), 2-bromopyridine (416 mg, 2.6 mmol), K2CO3 (994 mg, 7.2 mmol) and Pd(dppf)Cl2 (20 mg) in dioxane (8 mL) and H2O (2 mL) was stirred at 125° C. for 30 min. under microwave heating under N2. The catalyst was filtered, and the filtrate was acidified with 2N HCl to pH 5˜6. The solution was concentrated, and the residue was dissolved in MeOH and filtered. The filtrate was concentrated, and the residue was purified by prep-TLC to give the title compound (205 mg, Yield 42.9%). LCMS (m/z): 200.0 (M+1).

후처리

  1. temperatureheating under N2
  2. filtrationThe catalyst was filtered
  3. concentrationThe solution was concentrated
  4. dissolutionthe residue was dissolved in MeOH
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by prep-TLC

출처 및 근거

ORD 기록
ord-9c80a45b87834459a401f8590f85ee4e
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993555B2

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