Dimethylformamide → 1-(4-Fluorobenzyl)-2-(oxazol-2-yl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine

HRID 1432211Notes

Reaction equation

HRID 1432211 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[NH:18][C:9]2=[N:10][CH:11]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:13]=[C:8]2[CH:7]=1.[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1.[H-].[Na+].CN(C)C=O>O>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:18]2[C:9]3=[N:10][CH:11]=[C:12]([S:14]([CH3:17])(=[O:15])=[O:16])[CH:13]=[C:8]3[CH:7]=[C:6]2[C:2]2[O:1][CH:5]=[CH:4][N:3]=2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 225043982-(oxazol-2-yl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 99293371-(4-Fluorobenzyl)-2-(oxazol-2-yl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridineYield 34.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
22.5 °C

Procedure

A mixture of 2-(oxazol-2-yl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine (0.19 g), 4-fluorobenzyl bromide (0.16 g), sodium hydride (32 mg, 60% purity), and dimethylformamide (10 ml) was stirred at 15 to 30° C. for 30 minutes. To the reaction mixture was added water, and the precipitated crystals were filtered off and dissolved in ethyl acetate. The solution was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue (0.14 g) was recrystallized (ethyl acetate/hexane) to obtain 92 mg of the desired product.

Workup

  1. filtrationthe precipitated crystals were filtered off
  2. dissolutiondissolved in ethyl acetate
  3. dry with materialThe solution was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue (0.14 g) was recrystallized (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d48b9d9b0555437b91733bc64f9359bf
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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