Cesium carbonate → 1-Methyl-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]urea

HRID 1098314ノート

反応式

HRID 1098314 の反応式
I[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:71][NH:72][C:73]([NH2:75])=[O:74].[Cl-].[NH4+]>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].O1CCOCC1>[CH3:71][NH:72][C:73]([NH:75][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1)=[O:74]

参加物

8

反応物 5

HCID 10796Cesium carbonateHCID 11719MethylureaHCID 25517Ammonium ChlorideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 231568037-iodo-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

生成物 1

HCID 231568601-Methyl-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]urea収率 9.4%

試薬・触媒・溶媒 2

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

実験手順

0.5 ml of a 1,4-dioxane solution contained 20.8 mg (0.05 mmol) of the 7-iodo-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one obtained in Step A of Example 114; 2.2 mg (0.0025 mmol) of tris(dibenzylideneacetone)dipalladium; 4.2 mg (0.0075 mmol) of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene; 22.8 mg (0.07 mmol) of cesium carbonate, and 4.44 mg (0.06 mmol) of methylurea, was stirred at 110° C. overnight. Thereafter, the reaction solution was cooled to a room temperature, and a saturated ammonium chloride aqueous solution was then added thereto. The mixture was extracted with ethyl acetate, and the extract was then dried over anhydrous sodium sulfate. The extract was concentrated, and the obtained residue was then purified by thin-layer chromatography (methylene chloride:methanol=20:1), so as to obtain 1.7 mg (9%) of 1-methyl-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]urea in the form of a colorless solid.

後処理

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialthe extract was then dried over anhydrous sodium sulfate
  3. concentrationThe extract was concentrated
  4. customthe obtained residue was then purified by thin-layer chromatography (methylene chloride:methanol=20:1)

出典と根拠

ORDレコード
ord-c34fe47d39f3445597d2a9e435b0575a
出典データセット
uspto-grants-2012_03
特許番号
US08143274B2

反応ノート

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