Cesium carbonate → HCID 11197250、化合物

HRID 2240906ノート

反応式

HRID 2240906 の反応式
[F:1][C:2]([F:16])([F:15])[CH2:3][NH:4][C:5]1[CH:6]=[C:7]([C:13]#[N:14])[C:8]([C:11]#[N:12])=[CH:9][CH:10]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:24][C:25]([O:27][CH3:28])=[O:26]>CC#N>[C:13]([C:7]1[CH:6]=[C:5]([N:4]([CH2:3][C:2]([F:15])([F:16])[F:1])[CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:10]=[CH:9][C:8]=1[C:11]#[N:12])#[N:14]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 576337284-[(2,2,2-Trifluoroethyl)amino]-1,2-benzenedicarbonitrile

生成物 1

HCID 11197250HCID 11197250、化合物収率 58%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
85 °C

実験手順

A solution of 4-[(2,2,2-trifluoroethyl)amino]-1,2-benzenedicarbonitrile (0.020 g, 0.089 mmol) in MeCN (3 mL) was treated with Cs2CO3 (0.078 g, 0.24 mmol) and methyl bromoacetate (0.037 g, 0.24 mmol) and heated at 85° C. under nitrogen for 8 h. Upon cooling, the mixture was partitioned between EtOAc and water. The organic phase was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (20-100% CH2Cl2-hexanes gradient) and the product crystallized from CH2Cl2-hexanes to give 0.015 g (58% yield) of the title compound as a white solid: MS (ES) m/z 296 (M−1).

後処理

  1. temperatureUpon cooling
  2. customthe mixture was partitioned between EtOAc and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (20-100% CH2Cl2-hexanes gradient)
  7. customthe product crystallized from CH2Cl2-hexanes

出典と根拠

ORDレコード
ord-df18a62da7804610ba0b5c91541ba94e
出典データセット
uspto-grants-2010_05
特許番号
US07723385B2

反応ノート

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