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

HRID 241526ノート

反応式

HRID 241526 の反応式
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

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 866910465-(4-Bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrole2 回

生成物 1

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

試薬・触媒・溶媒 2

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

反応条件

温度
65 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-de48fac1d2d04dec84902e698edeb682
出典データセット
uspto-grants-2014_02
特許番号
US08653000B2

反応ノート

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