Water → HCID 10760196, compound

HRID 1533492Notes

Reaction equation

[CH2:1]([C:3]1([OH:18])[C:13]2[C:8](=[C:9]([O:15]C)[N:10]=[C:11]([I:14])[CH:12]=2)[CH2:7][O:6][C:5](=[O:17])[CH2:4]1)[CH3:2].[I-].[Na+].Cl[Si](C)(C)C.O.[O-]S([O-])=O.[Na+].[Na+].[Cl-].[Na+].O>C(#N)C>[CH2:1]([C:3]1([OH:18])[C:13]2[CH:12]=[C:11]([I:14])[NH:10][C:9](=[O:15])[C:8]=2[CH2:7][O:6][C:5](=[O:17])[CH2:4]1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a flame dried flask was added iodolactone (8) (0.33 g, 0.90 mmol) followed by dry acetonitrile (12 mL). Sodium iodide (0.22 g, 1.44 mmol) was added followed by chlorotrimethylsilane (0.18 mL, 1.44 mmol). The resulting mixture was stirred at 22° C. for 15 minutes at which point H2O (7.6 μL, 0.42 mmol) was added and the mixture was heated at 60° C. After 5 hours at 60° C. the mixture was poured into a 1:1 solution of 5% Na2SO3/Brine (75 mL) and then quickly extracted with EtOAc (6×75 mL). The organic layer was dried (MgSO4) and chromatographed (CH2Cl2:MeOH 95:5) to yield iodopyridone (9) as a white solid 0.19 g (61%): 1H NMR (300 MHz, CDCl3/CD3OD) δ 0.62 (t, J=7 Hz, 3H), 1.45-1.54 (m, J=7 Hz, 2H), 2.80 (d, J=14 Hz, 1H), 2.97 (d, J=14 Hz, 1H), 4.93 (d, J=15 Hz, 1H), 5.06 (d, J=15 Hz, 1H), 6.66 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 7.5, 35.6, 41.9, 61.6, 72.5, 94.4, 118.3, 121.1, 156.5, 162.6, 172.7; HRMS (EI) m/z calcd for C11H12INO4 (M+) 348.9811, found 348.9815 LRMS (EI) m/z 349 (M+), 331, 320, 303, 289, 278, 264, 250, 162, 150, 122, 94, 57.

Workup

customTo a flame dried flask
additionwas added
extractionquickly extracted with EtOAc (6×75 mL)
dry with materialThe organic layer was dried (MgSO4)
customchromatographed (CH2Cl2:MeOH 95:5)

Sources & evidence

ORD record: ord-2b772ade71d740cc85fbb295223da1bb
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06207832B1

Reaction notes

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