Cesium carbonate → N-(6-Methoxy-pyridazin-3-yl)-2,2-dimethyl-propionamide

HRID 226108

반응식

HRID 226108 반응식
Cl[C:2]1[N:3]=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[CH3:10][C:11]([CH3:16])([CH3:15])[C:12]([NH2:14])=[O:13].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:9][O:8][C:5]1[N:4]=[N:3][C:2]([NH:14][C:12](=[O:13])[C:11]([CH3:16])([CH3:15])[CH3:10])=[CH:7][CH:6]=1

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 12957TrimethylacetamideHCID 744033-Chloro-6-methoxypyridazineHCID 634876Binap, (A+-)-

생성물 1

HCID 68840920N-(6-Methoxy-pyridazin-3-yl)-2,2-dimethyl-propionamide수율 175.2%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

3-Chloro-6-methoxy-pyridazine (10.0 g, 69. 18 mmol) is mixed with 2,2-dimethyl-propionamide (8.40 g, 83.01 mmol), BINAP (2.15 g, 3.46 mmol), Cs2CO3 (33.8 g, 103.8 mmol) in dioxane (150 mL). It is degassed by passing N2 through for 10 min at rt. Pd2(dba)3 (3.16 g, 3.46 mmol) is then added and the resulting reaction is refluxed overnight. The reaction is cooled to rt, diluted with EtOAc (150 mL); filtered through silica gel; washed with EtOAc (2×150 mL). The filtrate is washed with H2O (2×300 mL); dried with MgSO4; filtered and concentrated. Purification of the crude material by chromatography gives the title compound (6.59 g, 31.53 mmol, 46%). 1H NMR (CDCl3): δ. 1.35 (s, 9H), 4.08 (s, 3H), 7.01 (d, J=9.7 Hz, 1H), 8.41 (d, J=9.7 Hz, 1H), 8.44 (bs, 1H) ppm. ES-MS (m/z): calcd for C10H15N3O2 (M+H)+: 210.3. found: 210.1.

후처리

  1. customIt is degassed
  2. customthrough for 10 min
  3. customat rt
  4. customthe resulting reaction
  5. temperatureis refluxed overnight
  6. filtrationfiltered through silica gel
  7. washwashed with EtOAc (2×150 mL)
  8. washThe filtrate is washed with H2O (2×300 mL)
  9. dry with materialdried with MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurification of the crude material by chromatography

출처 및 근거

ORD 기록
ord-d7cb36f3b524427992584efaf5ffbc39
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557103B2

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