Sodium Carbonate → 2-[1-Methyl-3-(trifluoromethyl)pyrazol-5-yl]-5-nitro-1,3-thiazole

HRID 1524245Notes

Reaction equation

HRID 1524245 reaction equation
Br[C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1.[CH3:10][N:11]1[C:15](B(O)O)=[CH:14][C:13]([C:19]([F:22])([F:21])[F:20])=[N:12]1.C(=O)([O-])[O-].[Na+].[Na+].CC(=O)OCC.[Cl-].[Na+].O>COCCOC.CCO.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:10][N:11]1[C:15]([C:2]2[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=2)=[CH:14][C:13]([C:19]([F:22])([F:21])[F:20])=[N:12]1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 182112-Bromo-5-nitrothiazoleHCID 120567131-Methyl-3-(trifluoroMethyl)pyrazole-5-boronic acidHCID 131718255Brine ethyl acetate

Product 1

HCID 667801512-[1-Methyl-3-(trifluoromethyl)pyrazol-5-yl]-5-nitro-1,3-thiazoleYield 13.5%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-bromo-5-nitrothiazole (209 mg, 1 mmol), (1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)boronic acid (194 mg, 1 mmol), tetrakis(triphenylphosphine)-palladium(0) (Pd(Ph3P)4, 57 mg) and sodium carbonate (212 mg) in 3 ml DME, 0.5 ml EtOH and 0.5 ml water was heated under Ar in microwave reactor at 110° C. for 30 min. The reaction mixture was worked up with EA/brine. Org. phase was concentrated and then subjected to silica gel flash chromatography (0-30% B; A: hexane; B: 50% EA in hexane) to furnish 37.5 mg of 2-[1-methyl-3-(trifluoromethyl)pyrazol-5-yl]-5-nitro-1,3-thiazole (65) as light yellow solid (yield: 13.5%; purity>90%).

Workup

  1. concentrationphase was concentrated

Sources & evidence

ORD record
ord-ec30b49398c340d3b52e48e0c7824a42
Source dataset
uspto-grants-2015_07
Patent number
US09079891B2

Reaction notes

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