(Diethylamino)sulfur trifluoride → 3-(5-Bromopyridin-2-yl)-3-fluorothietane 1,1-dioxide

HRID 1500298Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2(O)[CH2:11][S:10](=[O:13])(=[O:12])[CH2:9]2)=[N:6][CH:7]=1.C(N(S(F)(F)[F:21])CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([F:21])[CH2:11][S:10](=[O:13])(=[O:12])[CH2:9]2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of the product of step 2, Example 18 (0.3 g, 1.097 mmol, 1 eq) in methylene chloride (30 mL) is added diethylaminosulfur trifluoride (0.175 mL, 1.295 mmol, 1.1 eq) at −78° C. Resulting reaction mixture is stirred at −78° C. for 1 hour. The reaction mixture is quenched with aqueous bicarbonate solution (15 mL) and extracted with methylene chloride (3×20 mL). Combined organic layer dried over sodium sulphate and concentrated in vacuo. The crude compound is purified by column chromatography using (100-200 mesh silica). Desired compound is eluted in 10% ethyl acetate/hexane to afford title compound (0.15 g): 1H NMR (400 MHz, DMSO) δ: 4.77-4.86 (m, 2H), 4.94-5.05 (m, 2H), 7.62 (d, 1H, J=8.4 Hz), 8.21-8.24 (dd, 1H, J1=8.44 Hz, J2=2.12 Hz), 8.85 (s, 1H). LC-MS (m/z): [M+H] 281.9.

Workup

customResulting
customreaction mixture
customThe reaction mixture is quenched with aqueous bicarbonate solution (15 mL)
extractionextracted with methylene chloride (3×20 mL)
dry with materialCombined organic layer dried over sodium sulphate
concentrationconcentrated in vacuo
customThe crude compound is purified by column chromatography
washDesired compound is eluted in 10% ethyl acetate/hexane

Sources & evidence

ORD record: ord-58bfa0e2e44a499b9192d684ea6a2155
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206126B2

Reaction notes

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