Sodium Iodide → HCID 90408511, compound

HRID 1855069Notes

Reaction equation

CC1C=CC(S(O[CH2:12][C:13]23[CH2:20][CH2:19][C:16]([C:21]4[CH:26]=[C:25]([O:27][CH:28]5[CH2:33][CH2:32][CH2:31][CH2:30][O:29]5)[CH:24]=[C:23]([F:34])[CH:22]=4)([CH2:17][CH2:18]2)[O:15][CH2:14]3)(=O)=O)=CC=1.[I-:35].[Na+]>CC(C)=O>[F:34][C:23]1[CH:22]=[C:21]([C:16]23[CH2:17][CH2:18][C:13]([CH2:12][I:35])([CH2:20][CH2:19]2)[CH2:14][O:15]3)[CH:26]=[C:25]([O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[CH:24]=1

Participants

Conditions

Temperature: 78 °C

Procedure

A mixture of 36C (0.9 g, 1.84 mmol) and sodium iodide (3.8 g, 25.4 mmol) in acetone (15 mL) was stirred at 78° C. for 18 h. The reaction cooled to rt and filtered. The filtrate was concentrated in vacuo, taken up in DCM (10 mL) and filtered. The residual solid was washed with DCM (5 mL×2). The combined organic filtrates were concentrated in vacuo. The residual crude oil was purified by flash chromatography using a 0% to 30% gradient of EtOAc/hexane (15 min) to give the title compound (0.730 g, 1.64 mmol, 89% yield) as a white solid. 1H NMR (CDCl3) δ: 6.88 (t, J=1.7 Hz, 1H), 6.76 (ddd, J=10.1, 2.3, 1.6 Hz, 1H), 6.70 (dt, J=10.5, 2.3 Hz, 1H), 5.41 (t, J=3.1 Hz, 1H), 3.96-3.85 (m, 3H), 3.68-3.60 (m, 1H), 3.07 (s, 2H), 2.10-1.95 (m, 5H), 1.89-1.58 (m, 9H); 19F NMR (CDCl3) δ: −111.9 (s).

Workup

temperatureThe reaction cooled to rt
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
filtrationfiltered
washThe residual solid was washed with DCM (5 mL×2)
concentrationThe combined organic filtrates were concentrated in vacuo
customThe residual crude oil was purified by flash chromatography
customa 0% to 30% gradient of EtOAc/hexane (15 min)

Sources & evidence

ORD record: ord-37e1f68320fa4910a929c94527ea262c
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962660B2

Reaction notes

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