Potassium bis(trimethylsilyl)amide → HCID 118005488, compound

HRID 1478479Notes

Reaction equation

HRID 1478479 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13](=[O:25])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[C:6]([CH:11]=1)[C:7](OC)=[O:8].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1COCC1.O>[Br:1][C:2]1[CH:11]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:12][C:13](=[O:25])[C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:24])[F:23])[CH:16]=1)=[C:7]2[OH:8]

Participants

5

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 118005521Methyl 5-bromo-2-(2-(3-(trifluoromethyl)phenyl)acetamido)benzoate2×

Product 1

HCID 118005488HCID 118005488, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of methyl 5-bromo-2-(2-(3-(trifluoromethyl)phenyl)acetamido)benzoate (3.86 g, 9.28 mmol, Intermediate 5: step b) in THF (100 mL) at −78° C. was added KHMDS (0.5 M in toluene, 55.6 mL, 27.8 mmol) over 8 minutes. The resulting light yellow solution was stirred at −78° C. for 5 minutes, then was transferred to an ice bath and stirred for 1 hour 15 minutes. The mixture was diluted with water and extracted once with EtOAc. The aqueous phase was acidified to pH 2 by addition of 1 N aqueous HCl solution. A white precipitate formed upon acidification and was collected by vacuum filtration and air dried to afford the title compound as a white powder.

Workup

  1. customwas transferred to an ice bath
  2. stirringstirred for 1 hour 15 minutes
  3. extractionextracted once with EtOAc
  4. additionThe aqueous phase was acidified to pH 2 by addition of 1 N aqueous HCl solution
  5. customA white precipitate formed upon acidification
  6. filtrationwas collected by vacuum filtration and air
  7. customdried

Sources & evidence

ORD record
ord-9f955b1c10f9431991bd33a22c8b1f86
Source dataset
uspto-grants-2016_08
Patent number
US09403816B2

Reaction notes

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