1,2-Dimethoxyethane → HCID 73877973, compound

HRID 1394146Notes

Reaction equation

HRID 1394146 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[NH:10][C:11]([C:13]1[C:14]([CH3:20])=[N:15][N:16]([CH3:19])[C:17]=1[F:18])=[O:12].[CH3:21][O:22][N:23]=[CH:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>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>[F:9][C:4]1[C:3]([NH:10][C:11]([C:13]2[C:14]([CH3:20])=[N:15][N:16]([CH3:19])[C:17]=2[F:18])=[O:12])=[C:2]([C:28]2[CH:29]=[CH:30][C:25]([CH:24]=[N:23][O:22][CH3:21])=[CH:26][CH:27]=2)[CH:7]=[C:6]([F:8])[CH:5]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 22252919HCID 22252919, compoundHCID 71447105{4-[(Methoxyimino)methyl]phenyl}boronic acid

Product 1

HCID 73877973HCID 73877973, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×

Procedure

At room temperature, a mixture of 0.35 g (0.001 mol) of N-(2-bromo-4,6-difluorophenyl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, 0.06 g (0.00005 mol) of tetrakis-(triphenylphosphine)-palladium, 0.32 g (0.0018 mol) of 4-[(methoxyimino)methyl]phenylboronic acid and 10 ml of 1,2-dimethoxyethane is admixed with a solution of 0.5 g (0.0047 mol) of sodium carbonate in 3 ml of water. The reaction mixture is then heated to reflux temperature and kept at this temperature for 15 h. For work-up, the reaction mixture is stirred into 200 ml of water. The resulting precipitate is filtered off with suction and dried. The residue that remains is chromatographed on silica gel using the mobile phase cyclohexane:ethyl acetate=1:1. Concentration of the eluate gives 0.20 g (48% of theory) of N-{3,5-difluoro-4′-[(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide in the form of a solid of melting point 164 to 167° C.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureto reflux temperature
  3. filtrationThe resulting precipitate is filtered off with suction
  4. customdried
  5. customThe residue that remains is chromatographed on silica gel using the mobile phase cyclohexane

Sources & evidence

ORD record
ord-a06f4e897ec8485cb27fdf4db88b49fb
Source dataset
uspto-grants-2008_03
Patent number
US07348350B2

Reaction notes

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