Sodium Carbonate → [5''-(3-Aminomethyl-5-methyl-phenyl)-[2,2';4',3'']terpyridin-6'-yl]-ethyl-amine

HRID 1798509ノート

反応式

HRID 1798509 の反応式
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([CH3:9])[CH:8]=1.C([O-])([O-])=O.[Na+].[Na+].Br[C:20]1[CH:21]=[C:22]([C:26]2[CH:31]=[C:30]([NH:32][CH2:33][CH3:34])[N:29]=[C:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)[CH:27]=2)[CH:23]=[N:24][CH:25]=1>COCCOC.C(Cl)Cl.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]>[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:20]2[CH:21]=[C:22]([C:26]3[CH:31]=[C:30]([NH:32][CH2:33][CH3:34])[N:29]=[C:28]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)[CH:27]=3)[CH:23]=[N:24][CH:25]=2)[CH:6]=[C:7]([CH3:9])[CH:8]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 44135952(5''-Bromo-[2,2';4',3'']terpyridin-6'-yl)-ethylamineHCID 866336493-Aminomethyl-5-methyl-phenyl boronic acid

生成物 1

HCID 86633648[5''-(3-Aminomethyl-5-methyl-phenyl)-[2,2';4',3'']terpyridin-6'-yl]-ethyl-amine

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6344Dichloromethane溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a solution of 5″-(3-Aminomethyl-5-methyl-phenyl boronic acid (Intermediate B27) (2.0 eq, 0.303 mmol, 50 mg) and 2M Na2CO3 (2.0 eq, 0.303 mmol, 0.152 ml) in DME (1 ml) is added (5″-Bromo-[2,2′;4′,3″]terpyridin-6′-yl)-ethylamine (Ex. 1.24) (1 eq, 0.152 mmol, 54 mg) followed by [1,1′-Bis(diphenylphosphino)-ferrocene]dichloropalladium (II), complex with DCM (0.1 eq, 0.015 mmol, 12.3 mg). The reaction mixture is heated using microwave radiation at 90° C. for 90 minutes. The reaction mixture is dissolved in DCM and washed with water. The organic layer is washed with brine, dried over drying agent MgSO4, filtered and the organic solvent is reduced in vacuo. The residue is purified by reverse phase chromatography (Isolute™ C18, 0-20% acetonitrile in water—0.1% TFA). The appropriate fractions by HPLC are combined and concentrated in vacuo. The resulting residue is dissolved in MeOH and loaded onto a SCX-2 cartridge eluting with MeOH and 2M NH3 in MeOH. The methanolic ammonia fractions are combined, concentrated in vacuo and dried under vacuum to afford the title compound; [M+H]+ 397.

後処理

  1. temperatureThe reaction mixture is heated
  2. customat 90° C.
  3. customfor 90 minutes
  4. washwashed with water
  5. washThe organic layer is washed with brine
  6. customdried
  7. dry with materialover drying agent MgSO4
  8. filtrationfiltered
  9. customThe residue is purified by reverse phase chromatography (Isolute™ C18, 0-20% acetonitrile in water—0.1% TFA)
  10. concentrationconcentrated in vacuo
  11. dissolutionThe resulting residue is dissolved in MeOH
  12. washeluting with MeOH and 2M NH3 in MeOH
  13. concentrationconcentrated in vacuo
  14. customdried under vacuum

出典と根拠

ORDレコード
ord-395e8167343446f2907ccd2ec23dbd14
出典データセット
uspto-grants-2013_01
特許番号
US08343966B2

反応ノート

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