2-(Methylamino)ethanol → HCID 57537593, compound

HRID 1693719Notes

Reaction equation

HRID 1693719 reaction equation
[Br:1][C:2]1[C:3](Cl)=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[CH:9][N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:5]2=[N:6][CH:7]=1.[CH3:28][NH:29][CH2:30][CH2:31][OH:32]>>[Br:1][C:2]1[C:3]([N:29]([CH3:28])[CH2:30][CH2:31][OH:32])=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[CH:9][N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 57537472HCID 57537472, compound

Product 1

HCID 57537593HCID 57537593, compoundYield 66%

Conditions

Temperature
145 °C

Procedure

5-Bromo-4-chloro-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (94 mg, 0.201 mmol) was combined 2-(methylamino)ethanol (161 μL, 2.01 mmol) in a sealed tube and heated for 15 hours at 145° C. The crude product was purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes to afford 2-{[5-Bromo-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-methyl-amino}-ethanol (67 mg, 0.132 mmol, 66% yield) as a clear oil.

Workup

  1. customThe crude product was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-f025d7a0d6f2484281a9f716f6925f1c
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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