Trimethylsilylacetylene → HCID 14373291, 화합물

HRID 414552

반응식

HRID 414552 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.C[Si]([C:17]#[CH:18])(C)C>N1C=CC=CC=1.C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:17]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2)#[CH:18]

참가 물질

6

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 143732816-Bromo-3,4-dihydroquinolin-2(1H)-one

생성물 1

HCID 14373291HCID 14373291, 화합물

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 1049Pyridine용매HCID 8471Triethylamine용매

실험 절차

A mixture of 8.0 g of 6-bromo-3,4-dihydrocarbostyril, 6.95 g of trimethylsilylacetylene, 460 mg of bis(triphenylphosphine)palladium dichloride and 62 mg of cuprous iodide in 53 ml of pyridine and 11 ml of triethylamine was refluxed for 3 days. The solvent was removed under reduced pressure, 50 ml of methanol added along with 300 mg of potassium carbonate, and the mixture stirred under nitrogen for 18 hours. The solvent was removed under reduced pressure and the residue chromatographed on silica gel, eluting with 3% methanol in methylene chloride, giving a product of 6-ethynyl-3,4-dihydrocarbostyril, m.p. 182°-184° C.

후처리

  1. temperaturewas refluxed for 3 days
  2. customThe solvent was removed under reduced pressure, 50 ml of methanol
  3. additionadded along with 300 mg of potassium carbonate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue chromatographed on silica gel
  6. washeluting with 3% methanol in methylene chloride

출처 및 근거

ORD 기록
ord-5620a142c0124c1082c104c5c4d5667c
출처 데이터셋
uspto-grants-1988_12
특허 번호
US04792561

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