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

HRID 226108

反応式

HRID 226108 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d7cb36f3b524427992584efaf5ffbc39
出典データセット
uspto-grants-2009_07
特許番号
US07557103B2

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