Triphenylphosphine → HCID 22349593, 화합물

HRID 896083노트

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HRID 896083 반응식
[CH3:1][N:2]([CH3:19])[CH2:3]/[CH:4]=[CH:5]/[Sn](CCCC)(CCCC)CCCC.Br[C:21]1[CH:22]=[CH:23][C:24]([O:44][CH3:45])=[C:25]([C:27]([C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=3[F:43])=[CH:31][CH:30]=2)=[O:28])[CH:26]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>COCCOCCOC.Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:43][C:37]1[CH:38]=[C:39]([F:42])[CH:40]=[CH:41][C:36]=1[NH:35][C:32]1[CH:31]=[CH:30][C:29]([C:27]([C:25]2[CH:26]=[C:21](/[CH:5]=[CH:4]/[CH2:3][N:2]([CH3:1])[CH3:19])[CH:22]=[CH:23][C:24]=2[O:44][CH3:45])=[O:28])=[CH:34][CH:33]=1

참가 물질

7

반응물 3

HCID 11776TriphenylphosphineHCID 14660624HCID 14660624, 화합물HCID 22349575(5-Bromo-2-methoxy-phenyl)-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone

생성물 1

HCID 22349593HCID 22349593, 화합물수율 28%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 313Hydrochloric Acid용매HCID 8150Diglyme용매

실험 절차

Dimethyl-((E)-3-tributylstannanyl-allyl)-amine (213 mg, 0.57 mmol) and (5-bromo-2-methoxy-phenyl)-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone (200 mg, 0.475 mmol) are added to a solution of Pd(OAc)2 (10 mg, 0.047 mmol) and PPh3 (50 mg, 0.19 mmol) in diethylene glycol dimethyl ether (12 ml) and heated to 135 C under argon for 30 minutes. The reaction mixture is evaporated to dryness and purified via chromatography (SiO2, acetone/hexanes 6/4>1/0 followed by TBME/MeOH/NH3conc 100/0/0>90/10/1) to yield the crude product, which is dissolved in 2N HCl, washed with TBME and the aqueous phase made alkaline with saturated Na2CO3. Extraction with EtOAc and evaporation of the organic phase delivers the title compound, which was dissolved in acetone and filtered through a bed of SiO2 to give the desired product as yellow foam (55 mg; 28%).

후처리

  1. temperatureheated to 135 C under argon for 30 minutes
  2. customThe reaction mixture is evaporated to dryness
  3. custompurified via chromatography (SiO2, acetone/hexanes 6/4>1/0 followed by TBME/MeOH/NH3conc 100/0/0>90/10/1)
  4. customto yield the crude product, which
  5. washwashed with TBME
  6. extractionExtraction
  7. customwith EtOAc and evaporation of the organic phase
  8. dissolutionwas dissolved in acetone
  9. filtrationfiltered through a bed of SiO2

출처 및 근거

ORD 기록
ord-1bebb78e3e664d5c906575219a351025
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919336B2

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