Potassium Phosphate, Tribasic → HCID 86695924, 화합물

HRID 1398451노트

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HRID 1398451 반응식
Cl[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[F:12].[Cl:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[C:16]([F:23])[CH:15]=1.P([O-])([O-])([O-])=O.[K+].[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]>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=2[F:12])=[C:16]([F:23])[CH:15]=1

참가 물질

7

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 4193595(4-Chloro-2-fluorophenyl)boronic acidHCID 86695923Methyl 4-chloro-5-fluoropyridine-3-carboxylate

생성물 1

HCID 86695924HCID 86695924, 화합물수율 50.1%

시약·촉매·용매 3

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

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온도
80 °C

실험 절차

To a solution of methyl 4-chloro-5-fluoronicotinate (1.2 g, 6.33 mmol) in 1,4-dioxane (12 mL) and water (0.5 mL) was added (4-chloro-2-fluorophenyl)boronic acid (1.214 g, 6.96 mmol). The mixture was then purged with nitrogen gas for 5 min. Potassium phosphate, dibasic (2.205 g, 12.66 mmol) and PdCl2(dppf) (0.371 g, 0.506 mmol) were added and again the mixture was purged with N2 for 5 min. The reaction mixture was heated to 80° C. for 12 h. After cooling, water was added to and the mixture was extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography using hexane and ethyl acetate to afford methyl 4-(4-chloro-2-fluorophenyl)-5-fluoronicotinate (900 mg, 3.17 mmol, 50% yield) as a yellow solid. LC/MS (ESI) m/e 284.0 [(M+H)+, calcd for C13H9ClF2NO2 284.02]; LC/MS retention time (method D): tR=1.01 min.

후처리

  1. customThe mixture was then purged with nitrogen gas for 5 min
  2. customagain the mixture was purged with N2 for 5 min
  3. temperatureAfter cooling
  4. additionwater was added to and the mixture
  5. extractionwas extracted with ethyl acetate (3×25 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-48aceb7ed8454f6fb9fec8decdc7b651
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901305B2

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