Sodium Carbonate → HCID 86696253, compound

HRID 2175130Notes

Reaction equation

HRID 2175130 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:9])[C:5]([F:8])=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:18]2[CH:19]=[N:20][N:21](C(OC(C)(C)C)=O)[CH:22]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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:8][C:5]1[C:4]([F:9])=[CH:3][C:2]([C:18]2[CH:19]=[N:20][NH:21][CH:22]=2)=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 145496545-Bromo-2,3-difluoropyridineHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate

Product 1

HCID 86696253HCID 86696253, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

5-bromo-2,3-difluoropyridine (2.0 g, 10.31 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (3.03 g, 10.31 mmol), Na2CO3 (2.186 g, 20.62 mmol) and Pd(Ph3P)4 (1.191 g, 1.031 mmol) were dissolved in dioxane (20 ml). The mixture was bubbled with Ar for 10 min. The reaction was stirred at 100° C. for overnight, cooled and concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH=30/1) to afford the title compound as white solid (1.0 g, 53.5% yield). LCMS (method B): [M+H]+=182, tR=1.98 min.

Workup

  1. customThe mixture was bubbled with Ar for 10 min
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (DCM/MeOH=30/1)

Sources & evidence

ORD record
ord-d7a8ee584d674ced85ece71ce3e3ec71
Source dataset
uspto-grants-2015_06
Patent number
US09062045B2

Reaction notes

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