Sodium Carbonate → HCID 90099858, compound

HRID 2207286Notes

Reaction equation

HRID 2207286 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH3:11])=[CH:4][N:3]=1.[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O.O.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>[F:12][C:13]1[CH:18]=[C:17]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH3:11])=[CH:4][N:3]=2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 587641932-chloro-5-(MethoxyMethoxy)pyridine

Product 1

HCID 90099858HCID 90099858, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

200 mg (1.0 eq) of the obtained 2-chloro-5-(methoxymethoxy)pyridine was dissolved in N,N-dimethylformamide/H2O=5:1 (16 mL), 193 mg (1.2 eq) of (3-fluorophenyl)boronic acid, 48 mg (3 mol %) of Pd(PPh3)4 and 586 mg (4.0 eq) of Na2CO3 were added. After reacting with microwave reactor at 120° C. for 30 minutes, N,N-dimethylformamide was removed by concentrating under reduced pressure. After extracting with ethyl acetate, the extract was treated with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was separated by column chromatography (developing solvent, hexane:ethyl acetate=9:1) to obtain 220 mg of 2-(3-fluorophenyl)-5-(methoxymethoxy)pyridine.

Workup

  1. additionwere added
  2. customN,N-dimethylformamide was removed
  3. concentrationby concentrating under reduced pressure
  4. extractionAfter extracting with ethyl acetate
  5. additionthe extract was treated with anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was separated by column chromatography (developing solvent, hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-113c5a33252745a19857a0c9c22eb031
Source dataset
uspto-grants-2016_06
Patent number
US09376429B2

Reaction notes

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