Sodium hydride → HCID 57537668, compound

HRID 1693715Notes

Reaction equation

HRID 1693715 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[CH2:17][OH:18])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[N:6][C:5]2[NH:8][CH:9]=[C:10]3[C:4]=2[C:3]=1[O:18][CH2:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]3=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 57537545HCID 57537545, compound

Product 1

HCID 57537668HCID 57537668, compoundYield 2.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

[2-(5-Bromo-4-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-phenyl]-methanol (66 mg, 0.2 mmol) was dissolved in 5 mL DMF and NaH was added until the gas evolution stops. The mixture was stirred at 80° C. for 14 h. The reaction was concentrated and quenched with saturated ammonium chloride solution (2 mL) and water (2 mL). The mixture was applied to a Varian chemelut cartridge and eluted with ethyl acetate. The crude product was purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes followed by mass triggered reverse phase HPLC to afford the title compound (1.3 mg, 0.004 mmol, 2.2% yield over 2 steps). 1H NMR (500 MHz, MeCN-d3) δ 8.23 (s, 1H), 7.75 (m, 2H), 7.43 (m, 2H), 7.25 (t, J=7 Hz, 1H), 5.30 (s, 2H). MS: m/z 301.0/303.0 (M+H+).

Workup

  1. concentrationThe reaction was concentrated
  2. customquenched with saturated ammonium chloride solution (2 mL) and water (2 mL)
  3. washeluted with ethyl acetate
  4. customThe crude product was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-1b117ea575154e6c92593779d8a14a7e
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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