Cesium carbonate → HCID 59596015, compound

HRID 2264190Notes

Reaction equation

HRID 2264190 reaction equation
Br[C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]([NH2:13])=[N:6][C:7]=1[C:8]1[O:9][CH:10]=[CH:11][N:12]=1.CC1(C)C(C)(C)OB([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCOCC1>[N+:14]([C:4]1[CH:3]=[C:2]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[C:7]([C:8]2[O:9][CH:10]=[CH:11][N:12]=2)=[N:6][C:5]=1[NH2:13])([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 59595965HCID 59595965, compound

Product 1

HCID 59596015HCID 59596015, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

An oven-dried resealable Schlenk tube was charged with 5-bromo-3-nitro-6-(1,3-oxazol-2-yl)pyridin-2-amine (0.141 g, 0.49 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.203 g, 0.99 mmol), dioxane (5 mL) and a 2M aqueous solution of cesium carbonate (0.74 mL, 1.48 mmol). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex [PdCl2dppf.DCM] (0.024 g, 0.03 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was sealed and the mixture was stirred and heated in an oil bath to 95° C. After 20 hours, the mixture was cooled and partitioned between 2M aqueous hydrochloric acid and ethyl acetate. The aqueous phase was filtered through Celite® and the pH was adjusted to 5-6 with solid sodium hydroxide. The suspension was cooled in an ice bath and the precipitate was filtered, washed with water and dried to give the title compound (0.090 g, 65%) as a yellow solid.

Workup

  1. additionwas added
  2. customAfter three new cycles of evacuation-backfilling with argon, the Schlenk tube was sealed
  3. temperaturethe mixture was cooled
  4. custompartitioned between 2M aqueous hydrochloric acid and ethyl acetate
  5. filtrationThe aqueous phase was filtered through Celite®
  6. temperatureThe suspension was cooled in an ice bath
  7. filtrationthe precipitate was filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-30b6633b8eca4e4f879285080c7d4df1
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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