Trimethylsilylacetylene → 2-Nitro-5-((trimethylsilyl)ethynyl)pyridine

HRID 77852

반응식

HRID 77852 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].C(N(CC)C(C)C)(C)C>CN1CCCC1=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[N+:8]([C:5]1[CH:4]=[CH:3][C:2]([C:16]#[C:15][Si:12]([CH3:14])([CH3:13])[CH3:11])=[CH:7][N:6]=1)([O-:10])=[O:9]

참가 물질

7

반응물 3

HCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 8176205-Bromo-2-nitropyridine

생성물 1

HCID 580762652-Nitro-5-((trimethylsilyl)ethynyl)pyridine수율 45.1%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
65 °C

실험 절차

To a solution of 5-bromo-2-nitropyridine (1.00 g, 4.93 mmol) in N-methylpyrrolidinone (20 mL) were added trimethylsilyl acetylene (1.39 mL, 9.85 mmol), tetrakis(triphenylphosphine)palladium (0) (114 mg, 985 μmol), copper (I) iodide (37.5 mg, 197 μmol) and N,N-diisopropylethylamine (1.72 mL, 9.85 mmol) at room temperature, which was stirred under nitrogen atmosphere for 4 hours at 65° C. The reaction solution was partitioned into water and ethyl acetate at 0° C. The organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=6:1) to obtain the title compound (490 mg, 45%).

후처리

  1. customThe reaction solution was partitioned into water and ethyl acetate at 0° C
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationthe solvent was concentrated under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=6:1)

출처 및 근거

ORD 기록
ord-36630ba5535945a794beef2fc6b317d0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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