Sodium Iodide → HCID 66834656, compound

HRID 61846Notes

Reaction equation

Br[C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7](=[O:39])[C:8]4[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@@H:23]5[C@@H:27]([CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[O:26][C:25]([CH3:38])([CH3:37])[O:24]5)=[CH:17][C:9]=4[C:10]([CH3:16])([CH3:15])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.[I-:40].[Na+].CN(C)[C@@H]1CCCC[C@H]1N(C)C>O1CCOCC1.[Cu](I)I>[Si:30]([O:29][CH2:28][C@H:27]1[O:26][C:25]([CH3:37])([CH3:38])[O:24][C@@H:23]1[CH2:22][O:21][C:18]1[CH:19]=[CH:20][C:8]2[C:7](=[O:39])[C:6]3[C:5]4[C:13](=[CH:14][C:2]([I:40])=[CH:3][CH:4]=4)[NH:12][C:11]=3[C:10]([CH3:16])([CH3:15])[C:9]=2[CH:17]=1)([C:33]([CH3:34])([CH3:35])[CH3:36])([CH3:31])[CH3:32]

Participants

Conditions

Temperature: 110 °C

Procedure

Under nitrogen atmosphere, 3-bromo-8-[(4R,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy]-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound T22-1, 300 mg, 0.47 mmol), sodium iodide (147 mg, 0.94 mmol) and copper iodide (9.40 mg, 0.047 mmol) were dissolved in dioxane (1.00 ml), added with (1R,2R)—N,N,N′,N′-tetramethyl-cyclohexane-1,2-diamine (15.4 μl, 0.094 mmol), and then stirred at 110° C. for 16 hr. The residues obtained from the reaction solution after concentration under reduced pressure were purified by silica gel column chromatography (methylene chloride/methanol) to obtain the title compound (220 mg, 70%).

Workup

customThe residues obtained from the reaction solution
concentrationafter concentration under reduced pressure
customwere purified by silica gel column chromatography (methylene chloride/methanol)

Sources & evidence

ORD record: ord-81b4e633fb664487b4012b89b0d20676
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440922B2

Reaction notes

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