Triethylsilane → HCID 58558117, compound

HRID 1969692Notes

Reaction equation

HRID 1969692 reaction equation
[CH3:1][Si:2]([CH3:36])([CH3:35])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2[N:12]=[CH:13][C:14]3[N:15]([C:16]([CH:19]4[CH2:24][CH2:23][N:22](C(OCC5C=CC=CC=5)=O)[CH2:21][CH2:20]4)=[CH:17][N:18]=3)[C:10]=2[CH:9]=[CH:8]1.C([SiH](CC)CC)C>[Pd](Cl)Cl>[NH:22]1[CH2:21][CH2:20][CH:19]([C:16]2[N:15]3[C:10]4[CH:9]=[CH:8][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:36])([CH3:35])[CH3:1])[C:11]=4[N:12]=[CH:13][C:14]3=[N:18][CH:17]=2)[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 58557900HCID 58557900, compound

Product 1

HCID 58558117HCID 58558117, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 24290Palladium ChlorideCatalyst

Procedure

A solution of benzyl 4-(3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)piperidine-1-carboxylate (0.580 g, 1.15 mmol, prepared using R from 1-(benzyloxycarbonyl)piperidine-4-carboxylic acid (Matrix), S from Example #3 Step E, E with TFA, KKKK with PFPAA, D with NaOH, KK), TEA (0.03 mL, 0.229 mmol), palladium (II) chloride (0.020 g, 0.115 mmol) in triethylsilane (18.3 mL, 115 mmol) was heated at about 120° C. for about 8 h. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The product was purified by silica gel chromatography eluting with a gradient of 0-10% (90:9:1) (MeOH/DCM/DEA) in DCM to give 8-(piperidin-4-yl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine (0.234 g, 55%) as a brown oil: LC/MS (Table 1, Method b) Rt=1.93 min; MS m/z: 372 (M+H)+.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe product was purified by silica gel chromatography
  4. washeluting with a gradient of 0-10% (90:9:1) (MeOH/DCM/DEA) in DCM

Sources & evidence

ORD record
ord-c5f11f3069444ac9a0043167b6fe6c32
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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