Cesium carbonate → HCID 57633764、化合物

HRID 2240877ノート

反応式

HRID 2240877 の反応式
[F:1][CH2:2][CH2:3][NH:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:16])([F:15])[F:14])[CH:6]=1.FCCN(CCF)C1C=CC(C#N)=C(C(F)(F)F)C=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:43][C:44]([O:46][CH3:47])=[O:45]>C(#N)C>[C:9]([C:8]1[CH:11]=[CH:12][C:5]([N:4]([CH2:3][CH2:2][F:1])[CH2:43][C:44]([O:46][CH3:47])=[O:45])=[CH:6][C:7]=1[C:13]([F:14])([F:15])[F:16])#[N:10]

参加物

6

反応物 4

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetate2 回HCID 57633709HCID 57633709、化合物HCID 714198994-[Bis(2-fluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

生成物 1

HCID 57633764HCID 57633764、化合物収率 50%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
85 °C

実験手順

To a solution of a 6:1 mixture of 4-[(2-fluoroethyl)amino]-2-(trifluoromethyl)benzonitrile and 4-[bis(2-fluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (0.100 g) in acetonitrile (3 mL) was added Cs2CO3 (0.169 g, 0.52 mmol) and methyl bromoacetate (0.080 g, 0.52 mmol). The mixture was heated at 85° C. for 2 h. Upon cooling, additional methyl bromoacetate (0.080 g, 0.52 mmol) was added and heated at 85° C. for 8 h. Upon cooling, the mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by radial chromatography (10-80% EtOAc-hexanes gradient) to give 0.052 g (50% yield) of the desired product as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.62 (d, J=8.9 Hz, 1H), 6.92 (d, J=2.7 Hz, 1H), 6.76 (dd, J=8.9, 2.7 Hz, 1H), 4.68 (dt, J=47.0, 4.8 Hz, 2H), 4.21 (s, 2H), 3.81 (dt, J=25.6, 4.8 Hz, 2H), 3.78 (s, 3H).

後処理

  1. temperatureUpon cooling
  2. temperatureheated at 85° C. for 8 h
  3. temperatureUpon cooling
  4. customthe mixture was partitioned between ethyl acetate and water
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by radial chromatography (10-80% EtOAc-hexanes gradient)

出典と根拠

ORDレコード
ord-1abfc78a5a1346328a8fec1ca0fd3f4e
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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