Imidazole → 4-(3-((Tert-butyldimethylsilyl)oxy)-2,2-dimethylpropyl)-3-(trifluoromethyl)aniline

HRID 576145Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([CH3:13])([CH3:12])[CH2:10][OH:11])=[C:4]([C:14]([F:17])([F:16])[F:15])[CH:3]=1.N1C=CN=C1.[CH3:23][C:24]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])[CH3:25]>C(Cl)Cl>[Si:27]([O:11][CH2:10][C:9]([CH3:13])([CH3:12])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][C:4]=1[C:14]([F:15])([F:16])[F:17])([C:24]([CH3:26])([CH3:25])[CH3:23])([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 25 °C

Procedure

To a mixture of 3-(4-amino-2-(trifluoromethyl)phenyl)-2,2-dimethylpropan-1-ol (300 mg, 1.213 mmol) in DCM (150 mL) was added imidazole (124 mg, 1.820 mmol) and TBSCl (219 mg, 1.456 mmol). Then the mixture was stirred at 25° C. for 5 h. The mixture was filtered and the filtrate was concentrated. The crude material was purified by preparative TLC (PE/EA=2:1, Rf=0.5) to yield a light yellow solid of 4-(3-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpropyl)-3-(trifluoromethyl)aniline (350 mg, 0.930 mmol, 77.0% yield): 1H NMR (400 MHz, CD3Cl) δ: 7.14 (d, J=8.4 Hz, 1H), 6.86 (d, J=2.8 Hz, 1H), 6.70 (dd, J=2.8, 8.4 Hz, 1H), 3.20 (s, 2H), 2.62 (d, J=1.2 Hz, 2H), 0.87 (s, 9H), 0.73 (s, 6H), 0.00 (s, 6H); ES-LCMS m/z 362 (M+H).

Workup

filtrationThe mixture was filtered
concentrationthe filtrate was concentrated
customThe crude material was purified by preparative TLC (PE/EA=2:1, Rf=0.5)

Sources & evidence

ORD record: ord-b203e8b0f1b94dc2ae528a7c7cb372bb
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09035063B2

Reaction notes

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