Tetrabutylammonium Fluoride → HCID 59533946, compound

HRID 2167323Notes

Reaction equation

HRID 2167323 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:17]=[CH:16][C:11](/[C:12](/[NH2:15])=[N:13]/[OH:14])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[F-].[CH2:23]([N+](CCCC)(CCCC)CCCC)[CH2:24]CC>C1COCC1>[F:1][C:2]([F:20])([F:21])[C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]3[N:15]=[C:23]([CH3:24])[O:14][N:13]=3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 43150616HCID 43150616, compound

Product 1

HCID 59533946HCID 59533946, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Z)-4-(4-(Trifluoromethyl)phenoxy)-N′-hydroxybenzamidine (79 mg, 0.23 mmol) was placed under nitrogen and THF was added. Then tetrabutylammonium fluoride (67 μL, 0.23 mmol) was added dropwise and the solution was stirred at room temperature for 92 hours 40 minutes. The product was purified by column chromatography over silica gel (EtOAc/Hex 1:12) to give a white solid (9.0 mg, 12%). 1H NMR (500 MHz, CDCL3) δ(ppm): 2.66 (3H, s), 7.11-7.14 (4H, m), 7.62 (2H, d, J=8.4 Hz), 8.08 (2H, d, J=9.0 Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 12.61 (CH3), 119.0 (CH), 119.7 (CH), 122.9, 125.3, 126.0 (C, q, J=32.5 Hz), 127.5 (CH, q, J=3.8 Hz), 129.6 (CH), 158.7, 159.6, 167.9, 176.8. 19F (282 MHz, CDCL3) δ(ppm): −61.89 (3F, s). MS (FAB+): 321 (MH+). HRMS for C16H11F3N2O2 (MH+): calculated: 320.0773; found 320.0779.

Workup

  1. customThe product was purified by column chromatography over silica gel (EtOAc/Hex 1:12)

Sources & evidence

ORD record
ord-6596782d2d4e431db36b34b88e39b3c1
Source dataset
uspto-grants-2015_06
Patent number
US09045442B2

Reaction notes

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