Potassium Phosphate, Tribasic → Methyl 2-chloro-5-methylnicotinate

HRID 2382173노트

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HRID 2382173 반응식
Br[C:2]1[CH:3]=[N:4][C:5]([Cl:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:21]B(O)O.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:12][C:5]1[N:4]=[CH:3][C:2]([CH3:21])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 139377Methylboronic AcidHCID 2763343Methyl 5-bromo-2-chloronicotinate

생성물 1

HCID 11636946Methyl 2-chloro-5-methylnicotinate수율 87%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 22272177Toluene water용매

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온도
100 °C

실험 절차

To a solution of methyl 5-bromo-2-chloronicotinate (1.05 g, 4.19 mmol), K3PO4 (2.95 g, 13.90 mmol), methylboronic acid (0.32 g, 5.26 mmol) and tricyclohexylphosphine (0.11 g, 0.39 mmol) in toluene/water (16 ml/0.8 ml) under nitrogen atmosphere was added Pd(OAc)2 (0.04 g, 0.18 mmol). The mixture was heated at 100° C. overnight under nitrogen atmosphere. The reaction mixture was then cooled to room temperature and concentrated in vacuum. Ethyl acetate was added to the residue and this organic layer was washed with water, brine, dried over MgSO4, filtered and the solvent evaporated under vacuum to yield the desired product as a yellow oil. Yield=87%

후처리

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated in vacuum
  3. additionEthyl acetate was added to the residue
  4. washthis organic layer was washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated under vacuum

출처 및 근거

ORD 기록
ord-fed20cce1bcf4d6db64c93351143fcf6
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258308B2

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