Dimethylformamide → HCID 66519750, compound

HRID 533915Notes

Reaction equation

HRID 533915 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17]Cl)=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:17][C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 66519750HCID 66519750, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a round-bottomed flask was added 6-bromopyridin-3-ol (5.0 g), PMBCl (4.95 g), K2CO3 (7.93 g) and DMF (20 mL). The resultant mixture was stirred at r.t. overnight. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (50 mL×2). The combined organic layers was washed with water (20 mL×2), brine (20 mL×2), and dried over anhydrous Na2SO4. After filtration and evaporation of the solvent, the residue was recrystallized from ethyl acetate and petroleum ether to provide the subtitle compound. MS ESI+: m/z=294 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate (50 mL×2)
  2. washThe combined organic layers was washed with water (20 mL×2), brine (20 mL×2)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationAfter filtration and evaporation of the solvent
  5. customthe residue was recrystallized from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-4367e39f82814814ab492aa9bdc80cbe
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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