2-Chloroethyl methyl sulfide → 4-Bromo-2-isopropyl-7-(2-methylsulfanyl-ethylsulfanyl)-2H-phthalazin-1-one

HRID 1783716Notes

Reaction equation

[SH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Br:16])=[N:7][N:8]([CH:13]([CH3:15])[CH3:14])[C:9]2=[O:12])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:20][CH2:21][S:22][CH3:23]>CN(C=O)C>[Br:16][C:6]1[C:5]2[C:10](=[CH:11][C:2]([S:1][CH2:20][CH2:21][S:22][CH3:23])=[CH:3][CH:4]=2)[C:9](=[O:12])[N:8]([CH:13]([CH3:14])[CH3:15])[N:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of crude 7-mercapto-2-isopropyl-4-bromo-2H-phthalazin-1-one (0.40 g, 1.3 mmol) in DMF (8 ml), was added NaH (60%, 0.064 g, 1.6 mmol) portion-wise. After stirring for 5 min, chloroethyl methylsulfide (0.17 g, 1.6 mmol) was added dropwise. The mixture was heated to 60° C. for two hours, after which time the mixture was concentrated under vacuum and the residue was subjected to flash column chromatography (elution: 90% heptane, 10% EtOAc) to give the title compound (0.44 g, 54% yield) as a white solid. δH (400 MHz, DMSO), 8.03 (1H, d), 7.92 (1H, d), 7.81 (1 H, d), 5.26-5.15 (1H, m), 3.41 (2H, t), 2.78 (2H, t), 2.15 (3H, s), 1.36 (6H, d).

Workup

concentrationafter which time the mixture was concentrated under vacuum
washthe residue was subjected to flash column chromatography (elution: 90% heptane, 10% EtOAc)

Sources & evidence

ORD record: ord-20e7de7e885c432b9e6b3aef80ba8188
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501410B2

Reaction notes

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