Nitrogen → 2-Pyridyl-2-quinolylamine

HRID 432125노트

반응식

HRID 432125 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2OC2C=CC=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N#N>CCOCC.C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

참가 물질

10

반응물 5

HCID 947NitrogenHCID 104392-AminopyridineHCID 119282-ChloroquinolineHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 23676156Sodium t-butoxide

생성물 1

HCID 53401122-Pyridyl-2-quinolylamine

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To a 250-mL round-bottom flask were added 2-aminopyridine (2.30 g, 24.4 mmol), 2-chloroquinoline (4.0 g, 24.4 mmol), sodium tert-butoxide (3.29 g, 34.2 mmol), palladium (II) acetate (0.22 g, 0.98 mmol), bis(2-diphenylphosphinophenyl)ether (0.49 g, 0.91 mmol), and toluene (100 mL sparged with N2). The reaction mixture was heated at 105° C. for 18 h under an atm of N2. The reaction mixture was diluted with ether and THF, and washed with water. This solution was passed through a pad of celite to remove insoluble particles. The organic layer was dried over MgSO4. The crude product was purified by column chromatography eluting with 90:10 CH2Cl2/CH3CN. 2-Pyridyl-2-quinolylamine was isolated as an olive powder (4.66 g, 86%). Results of 1H NMR spectroscopy are consistent with the product. 1H NMR (300 MHz, CDCl3): δ 6.93 (m, 1H), 7.30 (d, J=8.8 Hz, 1H), 7.35 (t, J=7.4 Hz, 1H), 7.62 (m, 1H), 7.70 (m, 2H), 7.86 (d, J=8.4 Hz, 1H), 8.0 (m, 2H), 8.31 (m, 1H), 8.38 (d, J=8.5 Hz, 1H).

후처리

  1. washwashed with water
  2. customto remove insoluble particles
  3. dry with materialThe organic layer was dried over MgSO4
  4. customThe crude product was purified by column chromatography
  5. washeluting with 90:10 CH2Cl2/CH3CN

출처 및 근거

ORD 기록
ord-9827a8a3effb46ba9d3f4f4a03378bd6
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06661023B2

반응 노트

불러오는 중…