Iodoethane → HCID 58365227, compound

HRID 60294Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([O:7][C:8]2[C:16]3[C:15]4[CH:17]=[C:18]([C:21]#[N:22])[N:19]=[CH:20][C:14]=4[N:13]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:12]=3[N:11]=[CH:10][CH:9]=2)[CH2:2]1.I[CH2:32][CH3:33]>C(#N)C.C(=O)(O)[O-].[Na+].C(Cl)Cl>[CH2:32]([N:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([O:7][C:8]2[C:16]3[C:15]4[CH:17]=[C:18]([C:21]#[N:22])[N:19]=[CH:20][C:14]=4[N:13]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:12]=3[N:11]=[CH:10][CH:9]=2)[CH2:2]1)[CH3:33]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (R)-4-(piperidin-3-oxy)-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (84 mg, 0.20 mmol) in acetonitrile (1.0 mL) was added iodoethane (24 uL, 0.30 mmol), and the mixture was heated at 50° C. for 18 hours. The cooled reaction mixture was diluted with saturated aqueous sodium bicarbonate solution (50 mL) and methylene chloride (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 4 g, ISCO, 1-20% methanol in methylene chloride) to afford the title compound as a yellow oil, which was used in the next step without any further purification (46 mg, 51%).

Workup

customThe cooled reaction mixture
customThe organic layer was separated
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
custompurified flash chromatography (silica, 4 g, ISCO, 1-20% methanol in methylene chloride)

Sources & evidence

ORD record: ord-a9521d400dec4729a34ca18e5546b9dd
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440976B2

Reaction notes

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