Sodium Iodide → 6-Iodo-3-(4-piperidin-1-ylmethyl-phenyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole

HRID 1506040Notes

Reaction equation

Br[C:2]1[N:10]=[CH:9][C:8]2[NH:7][C:6]3[N:11]=[CH:12][C:13]([C:15]4[CH:20]=[CH:19][C:18]([CH2:21][N:22]5[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]5)=[CH:17][CH:16]=4)=[CH:14][C:5]=3[C:4]=2[CH:3]=1.CNCCNC.[I-:34].[Na+]>O1CCOCC1.ClCCl.[Cu]I>[I:34][C:2]1[N:10]=[CH:9][C:8]2[NH:7][C:6]3[N:11]=[CH:12][C:13]([C:15]4[CH:20]=[CH:19][C:18]([CH2:21][N:22]5[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]5)=[CH:17][CH:16]=4)=[CH:14][C:5]=3[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 6-bromo-3-(4-piperidin-1-ylmethyl-phenyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole (250 mg, 0.6 mmol), copper (I) iodide (23 mg, 0.12 mmol), N,N′-dimethyl-1,2-ethanediamine (0.013 mL, 0.12 mmol), and sodium iodide (360 mg, 2.4 mmol) in 1,4-dioxane was heated at 110° C. for 3 days. The reaction was diluted with dichloromethane (20 mL), filtered, and concentrated to afford a residue that was purified by flash chromatography (silica, 10 g column, Biotage, 0-10% methanol in (DCM containing 1% 2M ammonia in methanol)) to afford the title compound as an orange solid (280 mg, 100%).

Workup

filtrationfiltered
concentrationconcentrated
customto afford a residue that
customwas purified by flash chromatography (silica, 10 g column, Biotage, 0-10% methanol in (DCM containing 1% 2M ammonia in methanol))

Sources & evidence

ORD record: ord-e06946f6ceb5475a98b23f5899292ec9
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216980B2

Reaction notes

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