Sodium Carbonate → HCID 66865720, compound

HRID 240133

Reaction equation

HRID 240133 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:8]=1.Br[C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:19]2[CH:20]=[C:21]([NH2:22])[CH:23]=[CH:24][CH:25]=2)[CH:6]=[N:5][CH:4]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115623-BromoanilineHCID 38661613-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Product 1

HCID 66865720HCID 66865720, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

3-methoxypyridine-5-boronic acid pinacol ester (0.205 g, 0.872 mmol) and 3-bromoaniline (0.063 mL, 0.581 mmol) were combined in DME (3 mL) in a flame-dried, round-bottom flask. Na2CO3 (2M, 0.610 mL, 1.22 mmol) and Pd(PPh3)4 (0.02 g, 0.017 mmol) were added to the stirred solution. The reaction was refluxed overnight under argon flow, and subsequently cooled to room temperature. The solvent was removed under vacuum and the resulting residue was resuspended in CH2Cl2. The organic phase was dried over MgSO4, filtered, and concentrated under vacuum. The crude product was purified by flash silica column chromatography (0-5% MeOH/CH2Cl2). The purification was monitored by TLC. The solvent was removed under vacuum from fractions containing product, resulting in 0.067 g in 58% yield.

Workup

  1. temperatureThe reaction was refluxed overnight under argon flow
  2. customThe solvent was removed under vacuum
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by flash silica column chromatography (0-5% MeOH/CH2Cl2)
  7. customThe purification
  8. customThe solvent was removed under vacuum from fractions
  9. additioncontaining product
  10. customresulting in 0.067 g in 58% yield

Sources & evidence

ORD record
ord-9d5b9bfef8e64bbb9765cd6a9a502164
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Linked notes

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