Water → 4-(3-Methoxypyridin-2-yl)benzoic acid

HRID 1391428ノート

反応式

HRID 1391428 の反応式
Cl[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:10](=[O:13])([O-])[O-:11].[K+].[K+].O.[C:17](#N)[CH3:18]>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>[CH3:9][O:8][C:7]1[C:2]([C:18]2[CH:17]=[CH:7][C:6]([C:10]([OH:11])=[O:13])=[CH:5][CH:4]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 962WaterHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 1042522-Chloro-3-methoxypyridine

生成物 1

HCID 534262554-(3-Methoxypyridin-2-yl)benzoic acid収率 77%

試薬・触媒・溶媒 1

HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
160 °C

実験手順

4-bis(hydroxyl)boron-1-methylbenzoate (2.8 mmol; 582 mg) was dissolved in acetonitrile (2 ml) and added to a 5 ml microwave vessel. To the solution was 3.5 mmol of 2-chloro-3-methoxypyridine (482 mg), 34 mg of tetrakis(triphenylphosphine)palladium(0). After stirring until dissolution, 8.4 mmol of potassium carbonate (1.16 g) was added, followed by 1 ml of water. The mixture was then heated at 160° C. for 300 seconds. After reaction completion, the solvents were evaporated under vacuum. The residue was dissolved in 2N KOH and THF and heated for 10 min. After hydrolysis, the THF was evaporated and the basic layer was washed with EtOAC. The aqueous layer was then acidified and extracted 3 times with EtOAc. The organic layers were combined and washed with water and brine. After drying, filtration and evaporation, the residue was triterated with ether to give the desired product as a yellow solid (423 mg; 77%).

後処理

  1. additionadded to a 5 ml microwave vessel
  2. additionwas added
  3. customAfter reaction completion
  4. customthe solvents were evaporated under vacuum
  5. dissolutionThe residue was dissolved in 2N KOH
  6. temperatureTHF and heated for 10 min
  7. customAfter hydrolysis
  8. customthe THF was evaporated
  9. washthe basic layer was washed with EtOAC
  10. extractionextracted 3 times with EtOAc
  11. washwashed with water and brine
  12. customAfter drying
  13. filtrationfiltration and evaporation

出典と根拠

ORDレコード
ord-21eee09d2ac64122b82f3ed3fe65fb49
出典データセット
uspto-grants-2008_03
特許番号
US07338950B2

反応ノート

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