Cesium carbonate → 4-(1-(tert-butyldimethylsilyloxy)cyclopropyl)-N-(diphenylmethylene)-3-fluoroaniline

HRID 1842907노트

반응식

HRID 1842907 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH2:10][CH2:9]2)=[C:4]([F:19])[CH:3]=1.[C:20](=[NH:33])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CCOC(C)=O.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].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[Si:12]([O:11][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([N:33]=[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:3][C:4]=2[F:19])[CH2:10][CH2:9]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

참가 물질

8

반응물 3

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 70816354(1-(4-Bromo-2-fluorophenyl)cyclopropoxy)(tert-butyl)dimethylsilane

생성물 1

HCID 866721464-(1-(tert-butyldimethylsilyloxy)cyclopropyl)-N-(diphenylmethylene)-3-fluoroaniline수율 92.9%

시약·촉매·용매 4

HCID 634876Binap, (A+-)-촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To a degassed suspension of (1-(4-bromo-2-fluorophenyl)cyclopropoxy)(tert-butyl)dimethylsilane (4.0 g, 11.59 mmol, 1.0 eq) in toluene (50 mL), was added BINAP (0.261 g, 0.347 mmol, 0.03 eq), benzophenone imine (2.1 g, 11.59 mmol, 1.0 eq) followed by Cs2CO3 (5.64 g, 17.38 mmol, 1.5 eq) in a sealed tube, then was added Pd2(dba)3 (0.138 g, 0.15 mmol, 0.013 eq) and the mixture heated to 100° C. for 8 h. The reaction mixture was diluted with EtOAc (120 mL), washed with water (25 mL×2), brine (25 mL) and dried over Na2SO4 and the solvent was evaporated under vacuum to get 4-(1-(tert-butyldimethylsilyloxy)cyclopropyl)-N-(diphenylmethylene)-3-fluoroaniline (4.8 g) crude product as a yellow oil (TLC system: EtOAc/PE (1:49), Rf: 0.75).

후처리

  1. washwashed with water (25 mL×2), brine (25 mL)
  2. dry with materialdried over Na2SO4
  3. customthe solvent was evaporated under vacuum

출처 및 근거

ORD 기록
ord-a64b09dae5374eaa85f811ef580c3ca8
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946204B2

반응 노트

불러오는 중…