Water → HCID 10760196, compound

HRID 1013884Notes

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-9ea102579f6845b0abdf8218b093a690
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07982041B2

Reaction notes

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