Iodoethane → (S)-tert-butyl 1-(6-cyano-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrol-4-yl)piperidin-3-yl(ethyl)carbamate

HRID 60263Notes

Reaction equation

HRID 60263 reaction equation
[C:1]([C:3]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:7]3[N:20]=[CH:21][CH:22]=[C:23]([N:24]4[CH2:29][CH2:28][CH2:27][C@H:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:25]4)[C:6]=3[C:5]=2[CH:4]=1)#[N:2].[H-].[Na+].I[CH2:41][CH3:42]>O1CCCC1>[C:1]([C:3]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:7]3[N:20]=[CH:21][CH:22]=[C:23]([N:24]4[CH2:29][CH2:28][CH2:27][C@H:26]([N:30]([CH2:41][CH3:42])[C:31](=[O:37])[O:32][C:33]([CH3:34])([CH3:36])[CH3:35])[CH2:25]4)[C:6]=3[C:5]=2[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 67298963(S)-tert-butyl 1-(6-cyano-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrol-4-yl)piperidin-3-ylcarbamate

Product 1

HCID 58365157(S)-tert-butyl 1-(6-cyano-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrol-4-yl)piperidin-3-yl(ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-tert-butyl 1-(6-cyano-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-4-yl)piperidin-3-ylcarbamate (130 mg, 0.25 mmol) in tetrahydrofuran (2 mL) was added sodium hydride as a 60% dispersion in mineral oil (20 mg, 0.5 mmol) followed by iodoethane (0.06 mL, 0.75 mmol) and reaction mixture was stirred overnight at ambient temperature. The reaction was quenched with water (30 μL), diluted with ethyl acetate (50 mL) and washed with water (20 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified by flash chromatography (silica, 4 g, ISCO, 0-60% ethyl acetate in heptane) to afford the title compound as a colorless oil, which was used in the next step without any further purification (90 mg).

Workup

  1. customThe reaction was quenched with water (30 μL)
  2. additiondiluted with ethyl acetate (50 mL)
  3. washwashed with water (20 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography (silica, 4 g, ISCO, 0-60% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-4f55974500f14d7982792025190bf9f0
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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