Sodium Carbonate → HCID 67330329, compound

HRID 1668659Notes

Reaction equation

HRID 1668659 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[N:7][CH:8]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:19]1[N:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=2)[N:22]=[C:21]([NH:32][CH2:33][C:34]2[CH:42]=[CH:41][CH:40]=[C:39]3[C:35]=2[CH:36]=[CH:37][NH:38]3)[CH:20]=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]>[NH:38]1[C:39]2[C:35](=[C:34]([CH2:33][NH:32][C:21]3[CH:20]=[C:19]([C:5]4[CH:6]=[N:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=4)[N:24]=[C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=4)[N:22]=3)[CH:42]=[CH:41][CH:40]=2)[CH:36]=[CH:37]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27630875-Methoxypyridine-3-boronic AcidHCID 86633451HCID 86633451, compound

Product 1

HCID 67330329HCID 67330329, 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

A solution of 5-methoxypyridine-3-boronic acid pinacolester (1.2 eq, 0.24 mmol, 56.4 mg) in DME (1 ml) under an inert atmosphere of argon is treated with 2M sodium carbonate (2 eq, 0.4 mmol, 0.2 ml) and then stirred at room temperature for 15 minutes. To this mixture is added [6-chloro-2-(6-methyl-pyridin-2-yl)-pyrimidin-4-yl]-(1H-indol-4-ylmethyl)-amine (1 eq, 0.2 mmol, 70 mg) followed by PdCl2(dppf).DCM (0.1 eq, 0.02 mmol, 16.3 mg) and the reaction mixture is heated at 80° C. for 90 minutes. The mixture is dissolved in DCM and washed with water. The solvent is removed in vacuo and the crude product is purified by reverse phase column chromatography and the appropriate fractions are combined and concentrated in vacuo. The resulting residue is loaded onto a SCX-2 cartridge eluting with MeOH followed by 2M NH3 in MeOH. The methanolic ammonia fractions are concentrated in vacuo and dried under vacuum to afford the title compound [M+H]+=423.

Workup

  1. washwashed with water
  2. customThe solvent is removed in vacuo
  3. customthe crude product is purified by reverse phase column chromatography
  4. concentrationconcentrated in vacuo
  5. washeluting with MeOH
  6. concentrationThe methanolic ammonia fractions are concentrated in vacuo
  7. customdried under vacuum

Sources & evidence

ORD record
ord-27eeb2addca8445b9495b3e7a3ceefe3
Source dataset
uspto-grants-2011_08
Patent number
US07989458B2

Reaction notes

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