Carbon tetrabromide → HCID 12147030, compound

HRID 1836331Notes

Reaction equation

[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][S:7]([NH:10][C:11]2[C:12](=[O:22])[N:13]([CH2:18][CH2:19][CH2:20]O)[C:14]([CH3:17])=[CH:15][CH:16]=2)(=[O:9])=[O:8])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:45]>C(Cl)Cl>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][S:7]([NH:10][C:11]2[C:12](=[O:22])[N:13]([CH2:18][CH2:19][CH2:20][Br:45])[C:14]([CH3:17])=[CH:15][CH:16]=2)(=[O:9])=[O:8])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-(4-Chlorobenzylsulfonylamino)-6-methyl-1-(3-hydroxypropyl)pyridone (3-8) (292 mg, 0.8 mmol) was dissolved in 8 mL methylene chloride under a nitrogen atmosphere. Triphenylphosphine (250 mg, 0.96 mmol) was added, followed by 370 mg (1.12 mmol) carbon tetrabromide. The reaction mixture was cooled to 0° C. and held at that temperature for 16 hours. The solvent was evaporated in vacuo and the product purified by flash chromatography (50:50 ethyl acetate: hexanes) to afford 227 mg of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 2.25 (m, 2H), 2.39 (s, 3H), 3.50 (t, 2H), 4.28 (t, 2H), 4.27 (s, 2H), 5.93 (d, 1H), 7.20-7.31 (m, 5H).

Workup

customThe solvent was evaporated in vacuo
customthe product purified by flash chromatography (50:50 ethyl acetate: hexanes)

Sources & evidence

ORD record: ord-95e18ca3e9b6467fae0882d86d8368d7
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777431B2

Reaction notes

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