1,2-Dimethoxyethane → HCID 59475104, compound

HRID 450702Notes

Reaction equation

HRID 450702 reaction equation
Br[C:2]1[S:6][C:5]([CH2:7][CH:8]([NH:10][C:11]([C:13]2[C:14]([CH:19]([F:21])[F:20])=[N:15][N:16]([CH3:18])[CH:17]=2)=[O:12])[CH3:9])=[C:4]([Cl:22])[CH:3]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)(O)[O-].[Na+].C(COC)OC>O.C(OC(=O)C)C>[Cl:22][C:4]1[CH:3]=[C:2]([C:27]2[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=2)[S:6][C:5]=1[CH2:7][CH:8]([NH:10][C:11]([C:13]1[C:14]([CH:19]([F:21])[F:20])=[N:15][N:16]([CH3:18])[CH:17]=1)=[O:12])[CH3:9]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 2856454-Fluorophenylboronic acidHCID 516892Sodium BicarbonateHCID 59475102HCID 59475102, compound

Product 1

HCID 59475104HCID 59475104, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In a sulfonation flask a mixture containing of 207 mg (0.5 mmol) 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid[2-(5-bromo-3-chlorothiophen-2-yl)-1-methylethyl]amide, 90 mg (0.64 mmol) 4-fluorophenylboronic acid, 151 mg (1.8 mmol) sodiumbicarbonate, 36 mg (0.05 mmol) bistriphenylphosphine palladium dichloride, 10 ml dimethoxyethane and 5 ml of water is stirred at reflux for 6 hours. After cooling to ambient temperature ethylacetate and water is added and the organic layer separated and washed again twice with water. After drying (sodium sulphate) and distilling off the solvent in a water jet vacuum, the crude product is obtained. Purification is achieved by column chroma-tography over silicagel (eluent: ethylacetate/heptane 1:1). Yield: 180 mg (80% of theory) of a slightly brown oil (1H-NMR: 1.29/d/3H, 0.9/m/2H, 3.09/m/2H, 3.89/s/3H, 4.42/m/1H, 6.38/s (broad)/1H, 6.89/t/1H—CF2H, 7.05/m/2H, 7.48/m/2H, 7.89/s/1H).

Workup

  1. temperatureat reflux for 6 hours
  2. additionis added
  3. customthe organic layer separated
  4. washwashed again twice with water
  5. dry with materialAfter drying (sodium sulphate)
  6. distillationdistilling off the solvent in a water jet vacuum

Sources & evidence

ORD record
ord-2f110c6e3feb47c9808f6a559760cbbd
Source dataset
uspto-grants-2013_07
Patent number
US08486986B2

Reaction notes

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