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

HRID 880261

反応式

HRID 880261 の反応式
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]

参加物

7

反応物 3

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

生成物 1

HCID 157331752-(Pyridin-2-YL)benzoic acid収率 42.9%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
125 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9c80a45b87834459a401f8590f85ee4e
出典データセット
uspto-grants-2015_03
特許番号
US08993555B2

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