Tetrabutylammonium Fluoride → HCID 178421813, compound

HRID 2174009Notes

Reaction equation

HRID 2174009 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:13](=[O:14])[O:12][C:11]([C:19]3[N:23](COCC[Si](C)(C)C)[C:22]4[CH:32]=[CH:33][C:34]([C:36]#[N:37])=[CH:35][C:21]=4[N:20]=3)([C:15]([F:18])([F:17])[F:16])[C:5]2=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.CC1C=C2C(=O)OC(C3N(COCC[Si](C)(C)C)C4C=C(C#N)C=CC=4N=3)(C(F)(F)F)C2=C2C=1NC=C2.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.[Cl-].[Na+].O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:13](=[O:14])[O:12][C:11]([C:19]3[NH:23][C:22]4[CH:32]=[CH:33][C:34]([C:36]#[N:37])=[CH:35][C:21]=4[N:20]=3)([C:15]([F:18])([F:17])[F:16])[C:5]2=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2

Participants

6

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 86701597HCID 86701597, compoundHCID 86701598HCID 86701598, compound

Product 1

HCID 178421813HCID 178421813, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of a mixture of (±)-2-(5-methyl-3-oxo-1-(trifluoromethyl)-3,6-dihydro-1H-furo[3,4-e]indol-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile and (±)-2-(5-methyl-3-oxo-1-(trifluoromethyl)-3,6-dihydro-1H-furo[3,4-e]indol-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile (36 mg, 0.068 mmol) in THF (0.5 mL), TBAF (1M in THF, 1.37 mL, 1.37 mmol) was added. The reaction was stirred at 75° C. for 30 min. The reaction mixture was cooled to room temperature, diluted with brine, and the layers were separated. The aqueous layer was extracted with ethyl acetate and dried over Na2SO4. After concentration, the residue was purified via silica gel flash chromatography (heptanes/((30% EtOAc in CH2Cl2)=0 to 100%) to give the title compound. 1H NMR (400 MHz, ACETONITRILE-d3) δ ppm 10.09 (br. s., 1H), 8.06 (s, 1H), 7.70 (d, J=8.5 Hz, 1H), 7.58 (dd, J=8.5, 1.5 Hz, 1H), 7.54-7.57 (m, 1H), 7.53 (d, J=0.8 Hz, 1H), 7.00-7.04 (m, 1H), 2.63 (d, J=0.8 Hz, 3H). HRMS calcd. for C20H11F3N4O2 (M+H)+ 397.0907. found 397.0902.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration
  7. customthe residue was purified via silica gel flash chromatography (heptanes/((30% EtOAc in CH2Cl2)=0 to 100%)

Sources & evidence

ORD record
ord-5fa5fdf8e59f43c9b33e83cb9605aa1a
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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