Sodium hydride → 2-bromo-6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine

HRID 1628052Notes

Reaction equation

[Br:1][C:2]1[N:3]=[C:4]2[CH:10]=[C:9]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=4)[N:13]([CH3:22])[CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:25][Si:26]([CH2:29][CH2:30][O:31][CH2:32]Cl)([CH3:28])[CH3:27]>CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]2[CH:10]=[C:9]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=4)[N:13]([CH3:22])[CH:12]=3)[N:8]([CH2:32][O:31][CH2:30][CH2:29][Si:26]([CH3:28])([CH3:27])[CH3:25])[C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-Bromo-6-(5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazine (0.500 g, 1.40 mmol; Preparation #B.1) in DMF (15 mL) was cooled to about 0° C. and then treated with 60 wt % NaH (0.112 g, 2.80 mmol). The mixture was stirred for about 15 min at about 0° C. followed by the addition of SEMCl (0.372 mL, 2.10 mmol). The mixture was warmed to rt for about 15 min then was concentrated under reduced pressure and purified on a 40 g silica gel column eluting with DCM to provide 2-bromo-6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (0.61 g, 89%): LC/MS (Table 2, Method b) Rt=3.88 min; MS m/z 487 (M+H)+.

Workup

temperatureThe mixture was warmed to rt for about 15 min
concentrationthen was concentrated under reduced pressure
custompurified on a 40 g silica gel column
washeluting with DCM

Sources & evidence

ORD record: ord-bb144729c9ed4ea2b8e6991dbd9eb4f8
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785639B2

Reaction notes

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