Dimethylformamide → HCID 66657894, compound

HRID 420571Notes

Reaction equation

HRID 420571 reaction equation
Br[C:2]1[S:6][C:5]([N:7]2[CH2:12][CH:11]([CH3:13])[N:10]([CH2:14][CH2:15][O:16][C:17]3[CH:18]=[C:19]([CH2:24][C:25]([OH:27])=[O:26])[CH:20]=[CH:21][C:22]=3[CH3:23])[CH:9]([CH3:28])[CH2:8]2)=[N:4][CH:3]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=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.O>[F:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=1[C:2]1[S:6][C:5]([N:7]2[CH2:12][CH:11]([CH3:13])[N:10]([CH2:14][CH2:15][O:16][C:17]3[CH:18]=[C:19]([CH2:24][C:25]([OH:27])=[O:26])[CH:20]=[CH:21][C:22]=3[CH3:23])[CH:9]([CH3:28])[CH2:8]2)=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 2734335(2,5-Difluorophenyl)boronic acidHCID 66657784HCID 66657784, compound

Product 1

HCID 66657894HCID 66657894, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of [3-[2-[4-(5-bromothiazole-2-yl)-2,6-dimethyl piperazine-1-yl]ethoxy]-4-methylphenyl]acetic acid (400 mg), 2,5-difluorophenyl boronic acid (270 mg), tetrakis(triphenylphosphine) palladium (100 mg), 1M sodium carbonate (4.3 mL) and dimethylformamide (8 mL) was reacted with a microwave reaction device at 180° C. for 5 minutes. To the reaction solution was added water and extracted with chloroform. The organic layer was washed with water and brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel to give the title compound (369 mg). Yield: 87%.

Workup

  1. customwas reacted with a microwave reaction device at 180° C. for 5 minutes
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-1101cae777924bc6a3118739a3ce7bea
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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