Potassium Carbonate → 3-(Pyridin-3-yl)benzoic acid

HRID 415295노트

반응식

HRID 415295 반응식
B([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])(O)O.Br[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:4]2[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=2)[C:7]([OH:9])=[O:8])[CH:15]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 27339573-Carboxyphenylboronic acid

생성물 1

HCID 27955753-(Pyridin-3-yl)benzoic acid수율 83.7%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a solution of 3-boronobenzoic acid (1.5 g, 9 mmol) and 3-bromopyridine (1.5 g, 9.9 mmol) in acetonitrile (40 mL) and water (40 mL), potassium carbonate (5.5 g, 40 mmol), Bis(triphenylphosphine)palladium(II) chloride (400 mg, 0.37 mmol) was added. The mixture was stirred under reflux overnight. Then the hot suspension was filtered and concentrated to half of the original volume and washed with dichloromethane. The aquatic phase was adjusted to pH=3 with hydrochloric acid (1 M) and filtrated, washed with water. The residue was dried in vacuum to obtain 1.5 g of 3-(pyridin-3-yl)benzoic acid. Yield: 83%. LC-MS (ESI) m/z: 200 (M+1)+.

후처리

  1. temperatureunder reflux overnight
  2. filtrationThen the hot suspension was filtered
  3. concentrationconcentrated to half of the original volume
  4. washwashed with dichloromethane
  5. filtrationfiltrated
  6. washwashed with water
  7. customThe residue was dried in vacuum

출처 및 근거

ORD 기록
ord-813d26f59d694dd4a16e97d2962e7b22
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088760B2

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