Potassium Carbonate → HCID 86590134, 화합물

HRID 1840521노트

반응식

HRID 1840521 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][C:12]([CH3:26])([O:14][C:15]([NH:17][C@@H:18]([CH2:23][C:24]#[CH:25])[C:19]([O:21][CH3:22])=[O:20])=[O:16])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.[Cu](I)I.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>[CH3:13][C:12]([CH3:26])([O:14][C:15]([NH:17][C@@H:18]([CH2:23][C:24]#[C:25][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)[C:19]([O:21][CH3:22])=[O:20])=[O:16])[CH3:11]

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 782402-Bromo-5-nitropyridineHCID 11817013(S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-ynoate

생성물 1

HCID 86590134HCID 86590134, 화합물수율 65%

시약·촉매·용매 4

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

A mixture of 2-bromo-5-nitropyridine (10.0 g; 49.0 mmol), methyl (S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]pent-4-ynoate (13.34 g; 58.8 mmol), copper iodide (0.465 g; 2.5 mmol), potassium carbonate (13.6 g; 98.0 mmol) and dichlorobis(triphenylphosphine)palladium (1.7 g; 2.5 mmol) in 30 ml of anhydrous dimethylformamide (DMF) is heated for 4 hours at 60° C. under argon. The reaction mixture is taken up in 800 ml of ethyl acetate, washed with 2×400 ml of water, 400 ml of saturated hydrogen carbonate and 400 ml of brine, dried over sodium sulphate, filtered and then concentrated under reduced pressure. The residue obtained is purified on a column of silica, eluting with a cyclohexane/ethyl acetate gradient of from 0 to 20% ethyl acetate. 11 g of methyl (S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-5-(5-nitropyrid-2-yl)pent-4-ynoate is isolated.

후처리

  1. washwashed with 2×400 ml of water, 400 ml of saturated hydrogen carbonate and 400 ml of brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customis purified on a column of silica
  7. washeluting with a cyclohexane/ethyl acetate gradient of from 0 to 20% ethyl acetate

출처 및 근거

ORD 기록
ord-faa9066029644151b344ebe3cf4afd74
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06680329B2

반응 노트

불러오는 중…