Sodium Carbonate → HCID 67417570, compound

HRID 1630737Notes

Reaction equation

HRID 1630737 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12](B(O)O)[C:13]([F:16])=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][C:29]([F:32])([F:31])[F:30])=[N:25][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.COCCOC.O>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([C:21]2[CH:26]=[N:25][C:24]([O:27][CH2:28][C:29]([F:31])([F:32])[F:30])=[CH:23][CH:22]=2)[C:13]([F:16])=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 223919645-Bromo-2-(2,2,2-trifluoroethoxy)pyridineHCID 67416380HCID 67416380, compound

Product 1

HCID 67417570HCID 67417570, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

5-((tert-Butyldimethylsilyloxy)methyl)-2-fluoropyridin-3-ylboronic acid (0.400 g, 1.40 mmol) was placed into a flask with a mixture of DME/H2O (6 mL/2 mL). To the reaction mixture was added 5-bromo-2-(2,2,2-trifluoroethoxy)pyridine (0.358 g, 1.40 mmol), Na2CO3 (1.87 g, 17.6 mmol), and Pd(PPh3)4 (0.081 g, 0.07 mmol) and the reaction was allowed to stir at 80° C. overnight. The reaction was cooled to rt and concentrated. A solution of saturated NaHCO3 (5 mL) was added, and then this mixture was extracted with EtOAc (3×20 mL). The combined organic layer was then washed with saturated NaHCO3 (1×10 mL), brine (1×10 mL), dried (MgSO4), filtered, and concentrated. Purification by column chromatography (9:1 hexane:EtOAc) gave 5-((tert-butyldimethylsilyloxy)methyl)-2-fluoro-3-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)pyridine.

Workup

  1. temperatureThe reaction was cooled to rt
  2. concentrationconcentrated
  3. additionA solution of saturated NaHCO3 (5 mL) was added
  4. extractionthis mixture was extracted with EtOAc (3×20 mL)
  5. washThe combined organic layer was then washed with saturated NaHCO3 (1×10 mL), brine (1×10 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by column chromatography (9:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-804cdca326b34461bbb85747a270a1b1
Source dataset
uspto-grants-2014_07
Patent number
US08791147B2

Reaction notes

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