Cesium carbonate → 5-(4,4-Difluorocyclohex-1-en-1-yl)-1-methyl-1H-pyrazole

HRID 337786Notes

Reaction equation

HRID 337786 reaction equation
I[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][CH:3]=1.[F:8][C:9]1([F:24])[CH2:14][CH2:13][C:12](B2OC(C)(C)C(C)(C)O2)=[CH:11][CH2:10]1.C(=O)([O-])[O-].[Cs+].[Cs+].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.O>[F:8][C:9]1([F:24])[CH2:14][CH2:13][C:12]([C:2]2[N:6]([CH3:7])[N:5]=[CH:4][CH:3]=2)=[CH:11][CH2:10]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 133340655-Iodo-1-methyl-1H-pyrazoleHCID 593513932-(4,4-Difluorocyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 899625835-(4,4-Difluorocyclohex-1-en-1-yl)-1-methyl-1H-pyrazoleYield 94.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 39a by using 5-iodo-1-methyl-1H-pyrazole (1.90 g, 9.14 mmol), 2-(4,4-difluorocyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.00 g, 4.10 mmol), tetrakis(triphenylphosphine)palladium (0) (240 mg, 0.208 mmol), cesium carbonate (2.70 g, 8.29 mmol), 1,4-dioxane (10 mL) and water (5 mL), to yield the title compound (767 mg, 94%) as a colorless oil.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-aa0020b6641d43b7a609671b7bc6d39c
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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