2-Bromopyridine → HCID 58626645, compound

HRID 854587Notes

Reaction equation

HRID 854587 reaction equation
[CH3:1][O:2][C:3](=[O:37])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][C:24](B4OC(C)(C)C(C)(C)O4)=[CH:23][CH:22]=3)[O:18][C:19]=2[CH3:20])=[CH:8][C:7]=1[CH3:36].Br[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3](=[O:37])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:22]=[CH:23][C:24]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=4)=[CH:25][CH:26]=3)[O:18][C:19]=2[CH3:20])=[CH:8][C:7]=1[CH3:36]

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 10340Sodium CarbonateHCID 58626662HCID 58626662, compound

Product 1

HCID 58626645HCID 58626645, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

3-[2-Methyl-4-(2-{5-methyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-oxazol-4-yl}-ethoxy)-phenyl]-propionic acid methyl ester (167 mg; 0.328 mmol) is dissolved in anhydrous toluene (1 mL), degassed, and filled with nitrogen three times. [1,1′-Bis-(diphenylphosphino)ferrocene]dichloropalladium(II) (15 mg, 0.02 mmol), 2-bromopyridine (67 ul, 0.7 mmol), and sodium carbonate (150 uL, 10 M aqueous, 1.5 mmol) are added, and the degassing procedure is repeated. The reaction is heated to 100° C. and monitored by HPLC. Upon complete consumption of starting material, the reaction is allowed to cool to room temperature and diluted with ethyl acetate. Celite is added and the mixture is filtered and rinsed with more ethyl acetate and water. The solution is further diluted with water and the two phases are separated. The organic layer is washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated.

Workup

  1. customdegassed
  2. additionfilled with nitrogen three times
  3. customUpon complete consumption of starting material
  4. temperatureto cool to room temperature
  5. additiondiluted with ethyl acetate
  6. additionCelite is added
  7. filtrationthe mixture is filtered
  8. washrinsed with more ethyl acetate and water
  9. additionThe solution is further diluted with water
  10. customthe two phases are separated
  11. washThe organic layer is washed with water and brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-617b46b34dc248e9b4b0e693782267ed
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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