HCID 57537593, compound → HCID 57537533, compound

HRID 1693723Notes

Reaction equation

HRID 1693723 reaction equation
[Br:1][C:2]1[C:3]([N:27]([CH3:31])[CH2:28][CH2:29][OH:30])=[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](COCC[Si](C)(C)C)[C:5]2=[N:6][CH:7]=1>FC(F)(F)C(O)=O.ClCCl>[Br:1][C:2]1[C:3]([N:27]([CH3:31])[CH2:28][CH2:29][OH:30])=[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][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 57537593HCID 57537593, compound

Product 1

HCID 57537533HCID 57537533, compoundYield 14.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
23 °C

Procedure

2-{[5-Bromo-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-methyl-amino}-ethanol (10 mg, 0.0197 mmol) was dissolved in a solution of trifluoroacetic acid (1 mL) and dichloromethane (1 mL) and stirred at 23° C. for 1.5 hours. The solvent was evaporated and the resulting oil was dissolved in 1 mL DMSO and 100 μL ethylenediamine and purified by mass triggered reverse phase HPLC to afford 2-{[5-Bromo-3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-methyl-amino}-ethanol (1.1 mg, 0.00266, 13% yield). 1H-NMR [500 MHz, d6-DMSO] δ: 8.14 (s, 1H), 7.31 (m, 1H), 7.27 (s, 1H) 7.21 (dd, 1H), 7.02 (d, 1H), 6.96, (td, 1H), 6.67, (s, 5H), 3.14 (t, 2H), 2.75 (s, 4H); MS [MH+] m/z: 376, 378.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe resulting oil was dissolved in 1 mL DMSO
  3. custom100 μL ethylenediamine and purified by mass triggered reverse phase HPLC

Sources & evidence

ORD record
ord-d22d7a6d3eb54bccace78c6ae5c5bbb1
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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