1,2-Dimethoxyethane → Tert-Butyl-[5''-(3-methoxy-phenyl)-[2,2';4',3'']terpyridin-6'-yl]-amine

HRID 1798494Notes

Reaction equation

HRID 1798494 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[C:18]([NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])[N:17]=[C:16]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[CH:15]=2)[CH:11]=[N:12][CH:13]=1.CO[CH2:33][CH2:34][O:35][CH3:36]>C(Cl)Cl>[C:21]([NH:20][C:18]1[N:17]=[C:16]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[CH:15]=[C:14]([C:10]2[CH:11]=[N:12][CH:13]=[C:8]([C:10]3[CH:9]=[CH:8][CH:13]=[C:34]([O:35][CH3:36])[CH:33]=3)[CH:9]=2)[CH:19]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 68737214(5''-Bromo-[2,2';4',3'']terpyridin-6'-yl)-tert-butyl-amine

Product 1

HCID 68736706Tert-Butyl-[5''-(3-methoxy-phenyl)-[2,2';4',3'']terpyridin-6'-yl]-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-Methoxy boronic acid (1.2 eq, 0.252 mmol, 32 mg) and 2M Na2CO3 (1 eq, 0.21 mmol, 0.1 ml) in dry DME (1 ml) under an inert atmosphere of argon are added (5″-Bromo-[2,2′;4′,3″]terpyridin-6′-yl)-tert-butyl-amine (Example 2.48; Step 1) (1 eq, 0.21 mmol, 80 mg) and PdCl2dppf (0.1 eq, 0.021 mmol, 15 mg). The reaction mixture is heated using microwave radiation at 90° C. for 2 hours 30 mins. The reaction mixture is dissolved in DCM and washed with water. The organic solvent is reduced in vacuo and the residue is purified by reverse phase chromatography (Isolute™ C18, 0-40% 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]+ 411.

Workup

  1. temperatureThe reaction mixture is heated
  2. customat 90° C.
  3. customfor 2 hours
  4. custom30 mins
  5. washwashed with water
  6. customthe residue is purified by reverse phase chromatography (Isolute™ C18, 0-40% acetonitrile in water—0.1% TFA)
  7. concentrationconcentrated in vacuo
  8. dissolutionThe resulting residue is dissolved in MeOH
  9. washeluting with MeOH and 2M NH3 in MeOH
  10. concentrationconcentrated in vacuo
  11. customdried under vacuum

Sources & evidence

ORD record
ord-0f2478a8bb6a46d8a671bf429227e471
Source dataset
uspto-grants-2013_01
Patent number
US08343966B2

Reaction notes

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