Triethylamine → Ethyl 5-((trimethylsilyl)ethynyl)nicotinate

HRID 606798

반응식

HRID 606798 반응식
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[C:9](Br)[CH:8]=[N:7][CH:6]=1)[CH3:2].C(N(CC)CC)C.[CH3:20][Si:21]([C:24]#[CH:25])([CH3:23])[CH3:22]>C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[C:9]([C:25]#[C:24][Si:21]([CH3:23])([CH3:22])[CH3:20])[CH:8]=[N:7][CH:6]=1)[CH3:2]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 140785Ethyl 5-bromopyridine-3-carboxylate

생성물 1

HCID 67047749Ethyl 5-((trimethylsilyl)ethynyl)nicotinate수율 86%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178419050HCID 178419050, 화합물촉매HCID 8857Ethyl Acetate용매

실험 절차

A solution of ethyl-5-bromonicotinate (30 g, 130.40 mmol), triethylamine (78 mL) and ethyl acetate (130 mL) is degassed for 15 min. Add trimethylsilylacetylene (88.46 mL, 625.92 mmol), bis(triphenylphosphine)palladium (II) dichloride (4.57 g, 6.52 mmol) and copper (I) iodide (0.25 g, 1.30 mmol) and stir at 50° C. under-nitrogen for 16 h. Cool to room temperature, filter through diatomaceous earth, wash with ethyl acetate, and concentrate. Purify the residue by silica gel chromatography, eluting with 10:1 hexanes:ethyl acetate, to give the title compound (27.7 g, 86%).

후처리

  1. filtrationfilter through diatomaceous earth
  2. washwash with ethyl acetate
  3. concentrationconcentrate
  4. customPurify the residue by silica gel chromatography
  5. washeluting with 10:1 hexanes

출처 및 근거

ORD 기록
ord-6b54da0751cb4c979b9b53d0c5f2c2c5
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915424B2

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