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

HRID 736874
ノート
印刷プレビュー

反応式

HRID 736874 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
触媒
HCID 962Water溶媒
HCID 5223901,2-Dimethoxyethene溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ac784a410fa649ea88dc389a97ed845d
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07595405B2

反応ノート

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