3-Nitrophenylboronic Acid → HCID 11615843, 화합물

HRID 1059927노트

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HRID 1059927 반응식
Cl[C:2]1[N:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N+:12]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:7][O:6][C:4]([C:3]1[C:2]([C:19]2[CH:20]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=[CH:17][CH:18]=2)=[N:11][CH:10]=[CH:9][CH:8]=1)=[O:5]

참가 물질

7

반응물 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 819931Methyl 2-chloronicotinate

생성물 1

HCID 11615843HCID 11615843, 화합물수율 27.6%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a suspension of methyl 2-chloronicotinate (1.89 g), 3-nitrophenylboronic acid (1.67 g) and tetrakis(triphenylphosphine)-palladium (578 mg) in 1,2-dimethoxyethane (20 ml) was added 2M aqueous solution of sodium carbonate (11 ml). The mixture was stirred at 80° C. for 3 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was triturated with 2-propanol, filtered, washed with 2-propanol and dried under reduced pressure to give 3-(3-methoxycarbonylpyridin-2-yl)-nitrobenzene (713 mg).

후처리

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was triturated with 2-propanol
  7. filtrationfiltered
  8. washwashed with 2-propanol
  9. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-18acd4eb5d57410c809d64ec696146ae
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521643B1

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