Triethylamine → HCID 25030121, compound

HRID 1436447Notes

Reaction equation

HRID 1436447 reaction equation
FC(F)(F)S(O[C:7]1[N:8]=[C:9]([N:12]2[C:16]([CH3:18])([CH3:17])[CH2:15][O:14][C:13]2=[O:19])[S:10][CH:11]=1)(=O)=O.[F:22][C:23]([F:34])([F:33])[C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(N(CC)CC)C>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:18][C:16]1([CH3:17])[CH2:15][O:14][C:13](=[O:19])[N:12]1[C:9]1[S:10][CH:11]=[C:7]([C:27]2[CH:28]=[CH:29][C:24]([C:23]([F:34])([F:33])[F:22])=[CH:25][CH:26]=2)[N:8]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 86760990HCID 86760990, compound

Product 1

HCID 25030121HCID 25030121, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A vial under nitrogen was charged with 2-(4,4-dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl trifluoromethanesulfonate (100 mg, 0.28 mmol), [4-(trifluoromethyl)phenyl]-boronic acid (58 mg, 0.31 mmol), and tetrakis(triphenylphosphine)palladium (65 mg, 0.056 mmol) followed by tetrahydrofuran (0.6 mL) and triethylamine (0.13 mL, 0.92 mmol). The mixture was stirred for 16 h, diluted with tetrahydrofuran, passed through a plug of silica gel (2 g) and concentrated. The crude product was purified by reverse phase HPLC to give the title compound. HRMS: calcd for C15H13F3N2O2S+H+, 343.07226; found (ESI-FT/MS, [M+H]1+), 343.0725; Analytical HPLC: purity 100% at 210-370 nm, 10.7 min; 100% at 268 nm, 10.7 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-370fafb21f5a403a853c5fe6de980d00
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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