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Triethylamine → HCID 89657570, 화합물

HRID 1775200
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HRID 1775200 반응식
Br[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[CH2:14][N:15]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:16][C:17](=[O:19])[CH:18]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.C(Cl)Cl.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:19]=[C:17]1[C:18]2[C:2]3[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=3[NH:12][C:13]=2[CH2:14][N:15]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:16]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 89655469HCID 89655469, 화합물

생성물 1

HCID 89657570HCID 89657570, 화합물수율 72%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매
HCID 6342
Acetonitrile
용매
HCID 6344Dichloromethane용매

실험 절차

A mixture of benzyl 3-((2-bromo-3-(methoxycarbonyl)phenyl)amino)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (0.13 g, 0.28 mmol), palladium acetate (0.013 g, 0.06 mmol), tri-o-tolylphosphine (0.72 g, 0.19 mmol), and triethylamine (0.36 g, 0.36 mmol) in acetonitrile (2 mL) was heated in a sealed tubule flushed with nitrogen at 100° C. for 9 h. The cooled reaction mixture was diluted with DCM (3×50 mL) and water (10 mL). The organic layer was separated, washed with water, dried (Na2SO4), and concentrated. The remaining residue was chromatographed on silica gel, eluted with gradient 0-100% EtOAc in hexane to give the title compound (0.076 g, 72%). 1H NMR (CDCl3-d1) δ 9.62 (s, 1H), 7.24-7.50 (m, 8H), 5.18 (s, 2H), 4.88 (s, 2H), 4.27 (s, 2H), 3.98 (s, 3H). MS (ESI) m/e [M+1]+ 379.0.

후처리

  1. temperaturewas heated in a sealed
  2. customtubule flushed with nitrogen at 100° C. for 9 h
  3. customThe cooled reaction mixture
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe remaining residue was chromatographed on silica gel
  9. washeluted with gradient 0-100% EtOAc in hexane

출처 및 근거

ORD 기록
ord-8771289ab66e4be3af5afad683c28e2b
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09260440B2

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