Sodium Carbonate → HCID 54683964, compound

HRID 1817372Notes

Reaction equation

HRID 1817372 reaction equation
Br[C:2]1[N:11]([CH3:12])[C:10](=[O:13])[C:9]([OH:14])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=1)[C:7]2=[O:15].[N:25]1[CH:30]=[CH:29][CH:28]=[C:27](B(O)O)[CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[Cl:24][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[F:23])[CH2:16][N:6]1[CH2:5][CH2:4][C:3]2[C:8](=[C:9]([OH:14])[C:10](=[O:13])[N:11]([CH3:12])[C:2]=2[C:27]2[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=2)[C:7]1=[O:15]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 54702919HCID 54702919, compound

Product 1

HCID 54683964HCID 54683964, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-2-(3-chloro-4-fluorobenzyl)-8-hydroxy-6-methyl-2,3,4,6-tetrahydro-2,6-naphthyridine-1,7-dione (35 mg, 0.08 mmol; Example 80), tetrakis(triphenylphosphine)palladium(0) (5 mg), pyridine-3-boronic acid (15 mg, 0.13 mmol), aq sodium carbonate (2 M, 0.5 mL), and dioxane (1.5 mL) was heated in a microwave oven at 100° C. for 15 minutes. The product mixture was concentrated under vacuum, and the residue was partitioned between water and dichloromethane. The organic extract was separated, concentrated under vacuum. The residue was subjected to preparative reverse phase HPLC purification. Collection and lyophilization of appropriate fractions provide the titled compound.

Workup

  1. concentrationThe product mixture was concentrated under vacuum
  2. customthe residue was partitioned between water and dichloromethane
  3. extractionThe organic extract
  4. customwas separated
  5. concentrationconcentrated under vacuum
  6. customThe residue was subjected to preparative reverse phase HPLC purification
  7. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-3efca16e8cc04abc87c944419c56c09c
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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