2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine → HCID 66926038, compound

HRID 1808703Notes

Reaction equation

HRID 1808703 reaction equation
Br[C:2]1[N:3]=[C:4]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:6][CH:7]=1.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([CH3:32])[CH:28]([CH2:33][C:34]#[CH:35])[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([CH3:32])[CH:28]([CH2:33][C:34]#[C:35][C:2]2[N:3]=[C:4]3[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]3=[N:6][CH:7]=2)[CH2:27]1)=[O:25])([CH3:20])([CH3:22])[CH3:21]

Participants

3

Reactant 2

HCID 575165972-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazineHCID 86650158HCID 86650158, compound

Product 1

HCID 66926038HCID 66926038, compoundYield 85.5%

Procedure

2-Bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine (1.67 g, 5.09 mmol) and (+/−)-4-methyl-3-prop-2-ynyl-piperidine-1-carboxylic acid tert-butyl ester (1.21 g, 5.09 mmol) were reacted under the same conditions as described in example 4 above. The crude product was adsorbed onto silica (10 g) and purified by silica gel chromatography, eluting with 5% to 30% ethyl acetate in hexanes to afford 2.11 g of (+/−)-4-methyl-3-{3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-prop-2-ynyl}-piperidine-1-carboxylic acid tert-butyl ester as a yellow viscous oil. MS (M+H)+=485.

Workup

  1. custompurified by silica gel chromatography
  2. washeluting with 5% to 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b8e158b47c7f48efa4db1f17afd06ab1
Source dataset
uspto-grants-2013_01
Patent number
US08361962B2

Reaction notes

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