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Potassium Phosphate, Tribasic → 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester

HRID 736874
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HRID 736874 반응식
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=[C:6]([N+:19]([O-:21])=[O:20])[CH:5]=1.Br[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COC=COC.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:5]=[C:6]([N+:19]([O-:21])=[O:20])[CH:7]=[C:8]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]=2)[CH:9]=1
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참가 물질

7

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 5642162-Bromo-5-methylpyridineHCID 44119765Methyl 3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

생성물 1

HCID 578516583-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester수율 56.3%

시약·촉매·용매 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매
HCID 962Water용매
HCID 5223901,2-Dimethoxyethene용매

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온도
130 °C

실험 절차

To a solution of 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (100 mg, 0.326 mmol), 2-bromo-5 methyl-pyridine (56 mg, 0.326 mmol), K3PO4 (138 mg, 0.652 mmol) in dimethoxy ethylene (3 mL) and water (1 mL) was added Pd(Pph3)4 (11.3 mg, 0.001 mmol). The mixture was flushed with N2 and heated under microwave at 130° C. for 30 minutes. The reaction mixture was cooled, solvent was removed under reduced pressure, and the residue was purified by column chromatography (EtOAc/hexane=1:3) to afford 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (50 mg, 56%). MS (M+H)=273.

후처리

  1. customThe mixture was flushed with N2
  2. temperatureThe reaction mixture was cooled
  3. customsolvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography (EtOAc/hexane=1:3)

출처 및 근거

ORD 기록
ord-ac784a410fa649ea88dc389a97ed845d
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07595405B2

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