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Cesium carbonate → 4-fluoro-N-{[1-(4-methoxybenzyl)-2-oxo-6-(2-oxopyrrolidin-1-yl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}benzamide

HRID 1878019
ノート
印刷プレビュー

反応式

HRID 1878019 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:9](=[O:20])[O:8][C:7]([CH2:25][NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)([C:21]([F:24])([F:23])[F:22])[C:6]=2[CH:36]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:85]1[CH2:89][CH2:88][CH2:87][C:86]1=[O:90]>O1CCOCC1.C(OCC)(=O)C.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]>[F:34][C:31]1[CH:32]=[CH:33][C:28]([C:27]([NH:26][CH2:25][C:7]2([C:21]([F:24])([F:23])[F:22])[C:6]3[CH:36]=[C:2]([N:85]4[CH2:89][CH2:88][CH2:87][C:86]4=[O:90])[CH:3]=[CH:4][C:5]=3[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:9](=[O:20])[O:8]2)=[O:35])=[CH:29][CH:30]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 44549804N-{[6-bromo-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}-4-fluorobenzamide

生成物 1

HCID 68484957
4-fluoro-N-{[1-(4-methoxybenzyl)-2-oxo-6-(2-oxopyrrolidin-1-yl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}benzamide

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

A mixed solution of N-{[6-bromo-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}-4-fluorobenzamide (100 mg, 0.176 mmol), tris(dibenzylideneacetone)dipalladium (8.0 mg, 0.008 mmol), xantphos (15.2 mg, 0.024 mmol), cesium carbonate (57.4 mg, 0.176 mmol) and 2-pyrrolidinone (26.8 μL, 0.352 mmol) in dioxane (0.5 mL) was stirred at 120° C. for 30 minutes under microwave irradiation. After the reaction solution was left to cool, the solution was diluted with ethyl acetate and the organic layer was separated. The organic layer was washed with water and saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1), whereby the objective compound (69 mg, 69%) was obtained as a yellow oily substance.

後処理

  1. waitAfter the reaction solution was left
  2. temperatureto cool
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter the drying agent was removed by filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1), whereby the objective compound (69 mg, 69%)
  9. customwas obtained as a yellow oily substance

出典と根拠

ORDレコード
ord-c757652dac8d4e8294ce9fc77c09b318
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08314094B2

反応ノート

読み込み中…

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