Iodine → HCID 118274112, compound

HRID 522216Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:14]([CH3:15])[CH2:13][C:12]3[C:8]4[C:9](=[N:26][CH:27]=[CH:28][C:7]=4[C:6]=2[CH:29]=1)[N:10]([S:16]([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:11]=3.C([N-]C(C)C)(C)C.[Li+].[I:38]I>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:14]([CH3:15])[CH2:13][C:12]3[C:8]4[C:9](=[N:26][CH:27]=[CH:28][C:7]=4[C:6]=2[CH:29]=1)[N:10]([S:16]([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:17])=[O:18])[C:11]=3[I:38]

Participants

Conditions

Temperature: -75 °C

Procedure

To a solution of Example 41C (26.6 g, 65.3 mmol) in tetrahydrofuran (326 mL) at −75° C. under nitrogen was added lithium diisopropylamide (49.0 mL, 98 mmol) dropwise. A solution of iodine (33.1 g, 131 mmol) in 250 mL tetrahydrofuran was added dropwise and the mixture was stirred at −75° C. for 2 hours. The reaction was quenched with saturated aqueous sodium thiosulfate and extracted with ethyl acetate (twice). The combined organics were dried over magnesium sulfate, filtered and concentrated. The residue was slurried in hot 40% ethyl acetate in heptanes, cooled to room temperature and filtered and dried in vacuo to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.39 (d, J=5.3 Hz, 1H), 7.97 (d, J=8.4 Hz, 2H), 7.71 (d, J=10.3 Hz, 1H), 7.57 (d, J=5.4 Hz, 1H), 7.42 (d, J=8.3 Hz, 2H), 7.33-7.22 (m, 2H), 4.01 (s, 2H), 2.89 (s, 3H), 2.32 (s, 3H). MS (ESI+) m/z 534.0 (M+H)+.

Workup

customThe reaction was quenched with saturated aqueous sodium thiosulfate
extractionextracted with ethyl acetate (twice)
dry with materialThe combined organics were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
temperaturecooled to room temperature
filtrationfiltered
customdried in vacuo

Sources & evidence

ORD record: ord-d831426d624a4afc933de6350faa9c54
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328112B2

Reaction notes

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