Sodium Carbonate → HCID 86696252, compound

HRID 2175129Notes

Reaction equation

HRID 2175129 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:8])=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:17]2[CH:18]=[N:19][N:20](C(OC(C)(C)C)=O)[CH:21]=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[CH:4]=[CH:3][C:2]([C:17]2[CH:18]=[N:19][NH:20][CH:21]=2)=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27831685-Bromo-2-fluoropyridineHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate

Product 1

HCID 86696252HCID 86696252, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-2-fluoropyridine (1.0 g, 5.68 mmol) in dioxane (30 ml) was added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (1.671 g, 5.68 mmol), Na2CO3 (1.205 g, 11.36 mmol) and Pd(Ph3P)4 (0.657 g, 0.568 mmol). The reaction mixture was stirred at 100° C. under Ar atmosphere for overnight. The reaction was 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 (0.5 g, 44.2% yield). 1H-NMR (400 MHz, DMSO-d6) δ ppm 13.0 (s, 1H), 8.29 (s, 1H), 8.2 (d, 1H), 8.18 (d, 1H), 7.99 (s, 1H), 7.18 (dd, 1H). LCMS (method B): [M+H]+=164, tR=1.73 min.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (DCM/MeOH=30/1)

Sources & evidence

ORD record
ord-5b93630bd1084a6aa7264a6e71cce89c
Source dataset
uspto-grants-2015_06
Patent number
US09062045B2

Reaction notes

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