Diisopropylethylamine → 5-(1-(Tert-butyldimethylsilyloxy)propan-2-yl)-2-fluoropyridine

HRID 1812313Notes

Reaction equation

FC(F)(F)S([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])(=O)=O.[F:16][C:17]1[N:22]=[CH:21][C:20]([CH:23]([CH3:26])[CH2:24]O)=[CH:19][CH:18]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Si:7]([O:6][CH2:24][CH:23]([C:20]1[CH:19]=[CH:18][C:17]([F:16])=[N:22][CH:21]=1)[CH3:26])([C:10]([CH3:11])([CH3:12])[CH3:13])([CH3:8])[CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

Tert-butyldimethylsilyl trifluoromethanesulfonate (2.160 mL, 9.41 mmol) was added to a solution of 2-(6-fluoropyridin-3-yl)propan-1-ol (1.39 g, 8.96 mmol) and N,N-diisopropylethylamine (3.35 mL, 19.26 mmol) in CH2Cl2 (45 mL) at 0° C., and the resulting mixture stirred at 0° C. for 2.5 h. The reaction mixture was subsequently concentrated onto silica gel and chromatographically purified (silica gel, 0 to 20% EtOAc/hexanes) to provide 5-(1-(tert-butyldimethylsilyloxy)propan-2-yl)-2-fluoropyridine (1.89 g, 7.01 mmol, 78% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 8.06 (d, J=2.2 Hz, 1H), 7.65 (td, J=8.1, 2.5 Hz, 1H), 6.86 (dd, J=8.4, 2.9 Hz, 1H), 3.58-3.69 (m, 2H), 2.93 (sxt, J=6.7 Hz, 1H), 1.28 (d, J=7.0 Hz, 3H), 0.84 (s, 9H), −0.04 (s, 3H), −0.05 (s, 3H). 19F NMR (377 MHz, CDCl3) δ −72.06 (d, J=6.0 Hz, 1 F). m/z (ESI, +ve) 270.3 (M+H)+.

Workup

concentrationThe reaction mixture was subsequently concentrated onto silica gel
customchromatographically purified (silica gel, 0 to 20% EtOAc/hexanes)

Sources & evidence

ORD record: ord-49239a14d8924a70900119a8a3ebeffd
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362241B2

Reaction notes

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