Sodium Bicarbonate → HCID 9891398, compound

HRID 269405Notes

Reaction equation

HRID 269405 reaction equation
[C:1]([C:3]([NH:16][C:17](=[O:29])[C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=1)([CH3:15])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([F:13])=[CH:8][C:7]=1Br)#[N:2].[S:30]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31]1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[C:1]([C:3]([NH:16][C:17](=[O:29])[C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=1)([CH3:15])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([F:13])=[CH:8][C:7]=1[C:32]1[CH:33]=[CH:34][S:30][CH:31]=1)#[N:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 581760Thiophene-3-boronic acidHCID 24805528HCID 24805528, compound

Product 1

HCID 9891398HCID 9891398, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

120 mg of N-[2-cyano-1-(2-bromo-4,5-difluorophenoxy)-2-propyl]-4-trifluoromethoxybenzamide, 160 mg of thiophene-3-boronic acid and 3 ml of saturated aqueous sodium bicarbonate solution are dissolved in 4 ml of toluene and degassed for 15 minutes using a stream of nitrogen. Subsequently, 9 mg of tetrakis(triphenylphosphine)palladium are added and the mixture is stirred at reflux for 20 h. The mixture is subsequently diluted with ethyl acetate and washed with water and saturated sodium chloride solution. The organic phase is dried with magnesium sulfate, filtered and evaporated. After purifying by means of HPLC, the title compound is obtained with a melting point of 128-30° C.

Workup

  1. customdegassed for 15 minutes
  2. additionSubsequently, 9 mg of tetrakis(triphenylphosphine)palladium are added
  3. temperatureat reflux for 20 h
  4. additionThe mixture is subsequently diluted with ethyl acetate
  5. washwashed with water and saturated sodium chloride solution
  6. dry with materialThe organic phase is dried with magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customAfter purifying by means of HPLC

Sources & evidence

ORD record
ord-96509ab57564467a92d2cc48cf5a6e31
Source dataset
uspto-grants-2008_11
Patent number
US07446219B2

Reaction notes

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