Sodium Carbonate → 4-[3-(3,5-Dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]-2-methyl-benzaldehyde

HRID 241526노트

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HRID 241526 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][C:10]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[CH2:11][N:12]=2)=[CH:4][C:3]=1[CH3:25].[C:26]([O-])([O-])=[O:27].[Na+].[Na+].C([SiH](CC)CC)C>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:24][C:19]1[CH:18]=[C:17]([C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH:26]=[O:27])=[C:3]([CH3:25])[CH:4]=3)=[N:12][CH2:11]2)[CH:22]=[C:21]([Cl:23])[CH:20]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 866910465-(4-Bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrole2회

생성물 1

HCID 866910474-[3-(3,5-Dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]-2-methyl-benzaldehyde수율 74%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 6228Dimethylformamide용매

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온도
65 °C

실험 절차

To a solution of 5-(4-bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrole (i.e. the product of Step 4, 2.0 g) in dimethylformamide (DMF) (50 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (“Pd(dppf)Cl2”, 0.16 g), Na2CO3 (0.59 g) and triethylsilane (1.4 mL). The mixture was purged twice with N2, then purged three times with CO and stirred under an atmosphere of CO overnight at 65° C. Then, the reaction was concentrated in vacuum and purified by flash chromatography on silica gel to afford the title compound (1.32 g, 74%).

후처리

  1. customThe mixture was purged twice with N2
  2. custompurged three times with CO
  3. concentrationThen, the reaction was concentrated in vacuum
  4. custompurified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-de48fac1d2d04dec84902e698edeb682
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653000B2

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