Sodium Carbonate → HCID 68763594, compound

HRID 1798489Notes

Reaction equation

HRID 1798489 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11](B3OC(C)(C)C(C)(C)O3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C([O-])([O-])=O.[Na+].[Na+].[CH2:29]([NH:36][C:37]1[N:42]=[C:41]([C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([CH3:49])[N:44]=2)[CH:40]=[C:39]([C:50]2[CH:51]=[N:52][CH:53]=[C:54](Br)[CH:55]=2)[CH:38]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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]>[CH2:29]([NH:36][C:37]1[N:42]=[C:41]([C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([CH3:49])[N:44]=2)[CH:40]=[C:39]([C:50]2[CH:51]=[N:52][CH:53]=[C:54]([C:11]3[CH:10]=[CH:9][C:8]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]4)=[CH:13][CH:12]=3)[CH:55]=2)[CH:38]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 179989051-Methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazineHCID 68734156HCID 68734156, compound

Product 1

HCID 68763594HCID 68763594, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6344DichloromethaneSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 1-Methyl-4[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-phenyl]-piperazine (1.2 eq, 0.083 mmol, 0.025 g) and 2M Na2CO3 (4.0 eq, 0.138 mmol, 0.1 ml) in DME (1 ml) is added Benzyl-(5″-bromo-6-methyl-[2,2′;4′,3″]terpyridin-6′-yl)-amine (Example 2.40; step1) (1 eq, 0.069 mmol, 0.03 g) followed by [1,1′-Bis(diphenylphosphino)-ferrocene]dichloropalladium (II), complex with DCM (0.1 eq, 0.0069 mmol, 5 mg). The reaction mixture is heated using microwave radiation at 90° C. for 1 hour 15 mins. 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 crude residue is purified by reverse phase column chromatography (Isolute™ C18, 0-50% 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 followed by 2M NH3 in MeOH. The methanolic ammonia fractions are combined, concentrated in vacuo and dried under vacuum to afford the title compound; [M+H]+ 527.

Workup

  1. temperatureThe reaction mixture is heated
  2. customat 90° C.
  3. customfor 1 hour
  4. custom15 mins
  5. washwashed with water
  6. washThe organic layer is washed with brine
  7. customdried
  8. dry with materialover drying agent MgSO4
  9. filtrationfiltered
  10. customThe crude residue is purified by reverse phase column chromatography (Isolute™ C18, 0-50% acetonitrile in water—0.1% TFA)
  11. concentrationconcentrated in vacuo
  12. dissolutionThe resulting residue is dissolved in MeOH
  13. washeluting with MeOH
  14. concentrationconcentrated in vacuo
  15. customdried under vacuum

Sources & evidence

ORD record
ord-d6272a54c50b4bf29e35f874bc8ed23a
Source dataset
uspto-grants-2013_01
Patent number
US08343966B2

Reaction notes

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