Dichloromethane → 3-(6-Aminopyridin-2-yl)-4-methyl-N-[3-(trifloromethyl)phenyl]benzamide

HRID 77728

反応式

HRID 77728 の反応式
I[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH3:21])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)=[O:6].C([O-])(=O)C.[K+].CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1.C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+].Br[C:55]1[N:60]=[C:59]([NH2:61])[CH:58]=[CH:57][CH:56]=1>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].O.CN(C=O)C>[NH2:61][C:59]1[N:60]=[C:55]([C:2]2[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=2[CH3:21])[C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[O:6])[CH:56]=[CH:57][CH:58]=1

参加物

10

反応物 6

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 3008092-Amino-6-bromopyridineHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 171975693-iodo-4-methyl-N-(3-(trifluoromethyl)phenyl)benzamide

生成物 1

HCID 690476313-(6-Aminopyridin-2-yl)-4-methyl-N-[3-(trifloromethyl)phenyl]benzamide

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

To a degassed mixture of 3-iodo-4-methyl-N-[3-(trifluoromethyl)phenyl]benzamide (0.500 g, 1.23 mmol), potassium acetate (424 mg, 4.32 mmol), DMF (15 mL), and 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2]bi[[1,3,2]dioxaborolanyl] (0.329 g, 1.30 mmol) was added [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complex with DCM (1:1) (101 mg, 0.123 mmol). The reaction was heated to 80° C. for 3 hours, at which time conversion to the boronic ester was complete. The mixture was cooled and potassium carbonate (512 mg, 3.70 mmol), water (2.24 mL), and 6-bromopyridin-2-amine (214 mg, 1.23 mmol) were added. After degassing the mixture, it was heated to 85° C. for 1 hour. The solvent was then removed in vacuo. Water was added and the product was extracted with three portions of ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, and concentrated. Purification was carried out by flash column chromatography (eluting with a gradient from 0-50% ethyl acetate in hexanes) afforded the product. (254 mg, 50%).

後処理

  1. temperatureThe mixture was cooled
  2. customAfter degassing the mixture, it
  3. customThe solvent was then removed in vacuo
  4. additionWater was added
  5. extractionthe product was extracted with three portions of ethyl acetate
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customPurification
  10. washeluting with a gradient from 0-50% ethyl acetate in hexanes)
  11. customafforded the product

出典と根拠

ORDレコード
ord-fbb3af39a7c34521ab72c521080a6978
出典データセット
uspto-grants-2014_09
特許番号
US08841318B2

関連ノート

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