Cesium carbonate → HCID 57633764, 화합물

HRID 2240877노트

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HRID 2240877 반응식
[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]

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetate2회HCID 57633709HCID 57633709, 화합물HCID 714198994-[Bis(2-fluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

생성물 1

HCID 57633764HCID 57633764, 화합물수율 50%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
85 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1abfc78a5a1346328a8fec1ca0fd3f4e
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723385B2

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