Ethyl Acetate → HCID 58897692、化合物

HRID 2244979

反応式

HRID 2244979 の反応式
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1Br)[CH3:3].CC1(C)C(C)(C)OB([C:20]2[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=2)O1.C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>C1(C)C=CC=CC=1.CCCCO.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)[CH3:3]

参加物

9

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 747922-bromo-N,N-dimethylbenzylamineHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

生成物 1

HCID 58897692HCID 58897692、化合物収率 51.8%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 2631-Butanol溶媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒

実験手順

To a solution of 2-dimethylaminomethyl-bromobenzene (588 mg, 2.75 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (560 mg, 2.56 mmol) in toluene (10 mL) and n-BuOH (3 mL), Cs2CO3 (2.50 g, 7.67 mmol) in H2O (5 mL) was added, followed by addition of Pd(Ph3P)4 (200 mg, 0.17 mmol, 6%). The mixture was then heated at reflux for 4 h. EtOAc and H2O were added. The organic layer was separated, filtered, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel flash column using 50% EtOAc/hexanes (containing 1% TEA) as eluent to give a solid (300 mg). MS 182.0 (M—Me2N).

後処理

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 4 h
  3. customThe organic layer was separated
  4. filtrationfiltered
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel flash column

出典と根拠

ORDレコード
ord-da1e68709173428f9a05daab3eea05ba
出典データセット
uspto-grants-2010_03
特許番号
US07678913B2

関連ノート

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