Sodium Carbonate → HCID 86674222, compound

HRID 1425605Notes

Reaction equation

HRID 1425605 reaction equation
Br[C:2]1[CH:3]=[C:4]([N+:18]([O-:20])=[O:19])[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][O:16][CH3:17])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][N:23]=1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>CCOC(C)=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:21][C:22]1[N:23]=[CH:24][C:25]([C:2]2[CH:7]=[N:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([O:14][CH2:15][O:16][CH3:17])=[CH:10][CH:9]=3)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=2)=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 121772222-Fluoropyridine-5-boronic acid pinacol esterHCID 86674221HCID 86674221, compound

Product 1

HCID 86674222HCID 86674222, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-2-(4-(methoxymethoxy)phenyl)-3-nitropyridine (68 mg, 0.2 mmol), 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (45 mg, 0.2 mg), tetrakis(triphenylphosphine)palladium (12 mg, 0.01 mmol), Na2CO3 (0.5 mL, 1 M aqueous solution) and dioxane (1.5 mL) was heated at 100° C. for 10 min in a microwave reactor. After cooling to rt, the reaction was diluted with EtOAc (20 mL) and washed with brine (20 mL) and water (2×20 mL) and dried over MgSO4. Solvent was removed under reduced pressure and the residue was purified by silica chromatography (EtOAc in hexane, 5% to 40%) to afford 6′-fluoro-6-(4-(methoxymethoxy)phenyl)-5-nitro-3,3′-bipyridine as a yellow solid (48 mg, 67%). MS (ESI) m/z [M+H]+356.

Workup

  1. temperatureAfter cooling to rt
  2. washwashed with brine (20 mL) and water (2×20 mL)
  3. dry with materialdried over MgSO4
  4. customSolvent was removed under reduced pressure
  5. customthe residue was purified by silica chromatography (EtOAc in hexane, 5% to 40%)

Sources & evidence

ORD record
ord-8d70c2d2891547fb83f2a6471f86f5d8
Source dataset
uspto-grants-2015_01
Patent number
US08932557B2

Reaction notes

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