Potassium bis(trimethylsilyl)amide → HCID 54697511, compound

HRID 522377Notes

Reaction equation

HRID 522377 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:6]=1[C:7](OC)=[O:8])(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1COCC1.C1(C)C=CC=CC=1>[OH:8][C:7]1[C:6]2[C:5](=[CH:14][C:13]([C:15]([F:18])([F:17])[F:16])=[CH:12][CH:11]=2)[NH:4][C:1](=[O:3])[CH:2]=1

Participants

5

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 11701649Methyl 2-(acetylamino)-4-(trifluoromethyl)benzoate

Product 1

HCID 54697511HCID 54697511, compoundYield 64.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of step 2 (3.0 g) in THF (60 ml) was added 0.5 M KHMDS in toluene (108 ml) dropwise at −78° C. After the addition was completed, the mixture was kept at −78° C. for 40 minutes, then it was allowed to warm up slowly at room temperature. The mixture was quenched with H2O and the product was extracted twice with water. The combined aqueous layers were washed with ethyl acetate twice and then acidified with 6N HCl. The solid was filtered and the filter cake was washed with water and dried by vacuum aspiration to get a beige solid which was triturated into ethyl acetate to get a white solid (1.7 g). LRMS (ES+) m/z 230.05 (M+H)+.

Workup

  1. additionAfter the addition
  2. customThe mixture was quenched with H2O
  3. extractionthe product was extracted twice with water
  4. washThe combined aqueous layers were washed with ethyl acetate twice
  5. filtrationThe solid was filtered
  6. washthe filter cake was washed with water
  7. customdried by vacuum aspiration
  8. customto get a beige solid which
  9. customwas triturated into ethyl acetate

Sources & evidence

ORD record
ord-5e7d96a526b74e5eb29e922f2db7ffc0
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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