Cesium carbonate → HCID 10162554, 화합물

HRID 896082노트

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HRID 896082 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:12][CH:11]=2)=[O:9])[CH:7]=1.[CH3:27][N:28]1[CH2:33][CH2:32][N:31]([CH2:34][C:35]#[CH:36])[CH2:30][CH2:29]1.C([O-])([O-])=O.[Cs+].[Cs+].C(N(CC)C(C)C)(C)C>COCCOCCOC.CC(OC)(C)C.Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[NH:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]([C:6]2[CH:7]=[C:2]([C:36]#[C:35][CH2:34][N:31]3[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]3)[CH:3]=[CH:4][C:5]=2[O:25][CH3:26])=[O:9])=[CH:11][CH:12]=1

참가 물질

10

반응물 4

HCID 10796Cesium carbonateHCID 81531DiisopropylethylamineHCID 135140911-Methyl-4-(prop-2-yn-1-yl)piperazineHCID 22349575(5-Bromo-2-methoxy-phenyl)-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone

생성물 1

HCID 10162554HCID 10162554, 화합물수율 32%

시약·촉매·용매 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 313Hydrochloric Acid용매HCID 8150Diglyme용매HCID 15413tert-Butyl methyl ether용매

실험 절차

(5-Bromo-2-methoxy-phenyl)-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone (0.5 g; 1.18 mmol), 1-methyl-4-prop-2-ynyl-piperazine (0.33 g; 2.37 mmol), PdCl2(PPh3)2 (0.158 g; 0.22 mmol), Cs2CO3 (1.0 g; 3.1 mmol) and CuI (50 mg; 0.26 mmol) are dissolved in diethylene glycol dimethyl ether (10 ml) and N,N-diisopropylethylamine (5 ml) and heated to 140° C. for 1 hour. The reaction mixture is diluted with TBME, filtered, evaporated and purified by chromatography (SiO2, EtOAc/MeOH/NH3conc 100/0/0>90/10/1) to yield the crude title compound as brown foam. The latter is dissolved in 2N HCl, washed with EtOAc, Na2CO3 added to the aqueous phase and extracted with EtOAc. The organic phase is filtered through Alox and evaporated to give the pure product as yellow foam (177 mg; 32%).

후처리

  1. filtrationfiltered
  2. customevaporated
  3. custompurified by chromatography (SiO2, EtOAc/MeOH/NH3conc 100/0/0>90/10/1)
  4. customto yield the crude title compound as brown foam
  5. washwashed with EtOAc, Na2CO3
  6. additionadded to the aqueous phase
  7. extractionextracted with EtOAc
  8. filtrationThe organic phase is filtered through Alox
  9. customevaporated

출처 및 근거

ORD 기록
ord-c4d1e256d6fb4a36ba975b88c3925956
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919336B2

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