Trifluoroacetic acid → HCID 131735237, compound

HRID 626956Notes

Reaction equation

HRID 626956 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]([F:29])([F:28])[C:10]1([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:15][CH2:14][N:13]([C:16](OC(C)(C)C)=O)[CH2:12][CH2:11]1.C(=O)([O-])[O-].[Na+].[Na+].ClC1[N:42]=[CH:41][C:40]([B:43]([OH:45])[OH:44])=[CH:39][N:38]=1>>[CH2:26]([O:25][C:23]([C:10]1([C:9]([F:8])([F:28])[F:29])[CH2:11][CH2:12][N:13]([C:16]2[N:42]=[CH:41][C:40]([B:43]([OH:45])[OH:44])=[CH:39][N:38]=2)[CH2:14][CH2:15]1)=[O:24])[CH3:27]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 21054722HCID 21054722, compoundHCID 21747362(2-Chloropyrimidin-5-yl)boronic acid

Product 1

HCID 131735237HCID 131735237, compoundYield 89.3%

Procedure

TFA (5 mL) was added to 1-tert-butyl 4-ethyl 4-(trifluoromethyl)piperidine-1,4-dicarboxylate (0.42 g, 1.29 mmol). The mixture was stirred for 30 minutes, then rotary evaporated to dryness and left on a high vacuum line for 1 h. The residual syrup was dissolved in ethanol (4 mL), anhydrous sodium carbonate (0.35 g, 3.3 mmol) was added, and the mixture was stirred for 10 minutes. (2-Chloropyrimidin-5-yl)boronic acid (0.23 g, 1.4 mmol) was added and the reaction mixture was stirred at 60° C. for 6 h. The mixture was filtered through celite and concentrated to give the title compound (0.4 g, 89%) as an off-white foam, which was used without further purification. LCMS (pH 10) MH+ 348, RT 1.31 minutes.

Workup

  1. customrotary evaporated to dryness
  2. waitleft on a high vacuum line for 1 h
  3. dissolutionThe residual syrup was dissolved in ethanol (4 mL)
  4. stirringthe mixture was stirred for 10 minutes
  5. stirringthe reaction mixture was stirred at 60° C. for 6 h
  6. filtrationThe mixture was filtered through celite and
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-664108e02415475dbe9b2bea7e1e1e27
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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