2-Bromopyridine → HCID 66977380, compound

HRID 712166Notes

Reaction equation

HRID 712166 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5](B2OC(C)(C)C(C)(C)O2)=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=1.Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1.C([O-])([O-])=O.[K+].[K+].CCCCCC>C(#N)C.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:1][C:2]1[CH:3]=[CH:4][C:5]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:11])([CH3:12])[CH3:13])[CH:7]=1

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 8058HexaneHCID 11430Potassium CarbonateHCID 66976851HCID 66976851, compound

Product 1

HCID 66977380HCID 66977380, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(5-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pivalamide (23.4 g, 72.97 mmol) in acetonitrile (280 mL) was added 2-bromopyridine (16.14 g, 102.12 mmol) and aqueous solution of K2CO3 (50.40 g, 364.90 mmol). The reaction mixture was degassed by purging N2 for 15 min followed by addition of tetrakis(triphenylphosphine)palladium(0) (8.40 g, 7.30 mmol). The mixture was again degassed for 10-15 min then heated up to 80° C. for 8 h. After completion of reaction (by TLC), the mixture was poured into 100 mL of ice-cold water and extracted with EtOAc (3×250 mL). The combined organics were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 2.0% EtOAc:hexane to obtain the desired product as a colourless liquid (19.0 g, 96% yield).

Workup

  1. customThe reaction mixture was degassed
  2. customby purging N2 for 15 min
  3. customThe mixture was again degassed for 10-15 min
  4. customAfter completion of reaction (by TLC)
  5. extractionextracted with EtOAc (3×250 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe crude residue was purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-5e35f8efdc204e239b05fbe081693898
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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