Potassium Carbonate → 2-chloro-5-(4-chloro-6-quinolinyl)-N,N-dimethyl-3-pyridinamine

HRID 1963788노트

반응식

HRID 1963788 반응식
[Cl:1][C:2]1[C:7]([N:8]([CH3:10])[CH3:9])=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][N:3]=1.Br[C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[N:27]=[CH:26][CH:25]=[C:24]2[Cl:31].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:1][C:2]1[C:7]([N:8]([CH3:9])[CH3:10])=[CH:6][C:5]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[N:27]=[CH:26][CH:25]=[C:24]3[Cl:31])=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 51395376-Bromo-4-chloroquinolineHCID 582294462-chloro-N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine

생성물 1

HCID 446101612-chloro-5-(4-chloro-6-quinolinyl)-N,N-dimethyl-3-pyridinamine수율 71.2%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

(Some starting materials may be obtained from ECA International, Palatine, Ill.) To a microwave vial (5 mL), 2-chloro-N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine (0.110 g, 0.390 mmol), 6-bromo-4-chloroquinoline (0.102 g, 0.419 mmol), PdCl2 (dppf)-CH2Cl2 adduct (0.0183 g, 0.0224 mmol) and potassium carbonate (0.500 mL, 1.00 mmol) were added into 1,4-dioxane (3 mL). The mixture was degassed by bubbling nitrogen through for 10 min. The tube was irradiated with microwave at 100° C. for 10 min. The reaction was cooled to RT then partitioned between water (20 mL) and EtOAc (20 mL). The aqueous phase was extracted with EtOAc (2×20 mL). The combined organic phases were washed with saturated aqueous NaCl (40 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (eluent: acetone in hexanes 0% -30%) to afford the title compound as a white solid (0.0884 g). m/z: calc'd for C16H13Cl2N3; 317.0, found: 318.1 (M+1). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.97 (s, 6 H), 7.55-7.63 (m, 2 H), 7.98 (dd, J=8.8, 2.0 Hz, 1 H), 8.25 (d, J=8.8 Hz, 1 H), 8.38 (dd, J=5.3, 2.0 Hz, 2 H), 8.84 (d, J=4.7 Hz, 1 H).

후처리

  1. customThe mixture was degassed
  2. customby bubbling nitrogen through for 10 min
  3. customThe tube was irradiated with microwave at 100° C. for 10 min
  4. customthen partitioned between water (20 mL) and EtOAc (20 mL)
  5. extractionThe aqueous phase was extracted with EtOAc (2×20 mL)
  6. washThe combined organic phases were washed with saturated aqueous NaCl (40 mL)
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by column chromatography (eluent: acetone in hexanes 0% -30%)

출처 및 근거

ORD 기록
ord-5012a0c202e94f5aa07e558e46c99e36
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415376B2

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