Tetrabutylammonium Fluoride → HCID 66740014, compound

HRID 1627292Notes

Reaction equation

HRID 1627292 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:44]=[C:43]([F:45])[C:16]([CH2:17][S:18][C:19]2[N:20]([C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)[C:21]([C:24]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([O:34][CH3:35])[CH:28]=3)([CH3:26])[CH3:25])=[CH:22][N:23]=2)=[C:15]([Cl:46])[CH:14]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:46][C:15]1[CH:14]=[C:13]([CH:44]=[C:43]([F:45])[C:16]=1[CH2:17][S:18][C:19]1[N:20]([C:36]2[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=2)[C:21]([C:24]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[C:29]([O:34][CH3:35])[CH:28]=2)([CH3:26])[CH3:25])=[CH:22][N:23]=1)[O:12][CH2:11][CH2:10][CH2:9][OH:8]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66740288HCID 66740288, compound

Product 1

HCID 66740014HCID 66740014, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-(3-(tert-Butyldimethylsilyloxy)propoxy)-2-chloro-6-fluorobenzylthio)-5-(2-(4-fluoro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (750 mg, 1.08 mmol) in THF (10 mL) was added dropwise TBAF (1.0M in THF, 0.54 mL, 0.54 mmol). After the reaction was complete, it was quenched by addition of AcOH (0.5 mL). The mixture was evaporated in vacuo and the residue was purified by flash chromatography (EtOAc/Hex=1:2) to give the title compound (592 mg, 95%). 1H NMR (400 MHz, CDCl3) δ 7.29-7.26 (m, 1H), 7.21 (d, J=0.96 Hz, 1H), 6.91-6.84 (m, 1H), 6.76 (dt, J=8.18, 0.81 Hz, 3H), 6.70-6.65 (m, 1H), 6.58 (d, J=8.03 Hz, 1H), 6.52-6.43 (m, 2H), 6.38-6.30 (m, 2H), 4.15 (s, 3H), 4.06 (t, J=5.98 Hz, 3H), 3.84 (t, J=5.89 Hz, 2H), 3.79 (t, J=10.73 Hz, 4H), 2.13-1.97 (m, 4H), 1.48 (s, 8H).

Workup

  1. customit was quenched by addition of AcOH (0.5 mL)
  2. customThe mixture was evaporated in vacuo
  3. customthe residue was purified by flash chromatography (EtOAc/Hex=1:2)

Sources & evidence

ORD record
ord-e60dd2eea1bf41bda47441fd07b9c99c
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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