Sodium Hydroxide → ethyl (6-iodo-3-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-3H-imidazo[4,5-b]pyridin-2-yl)carbamate

HRID 706489Notes

Reaction equation

HRID 706489 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[NH:5][C:6]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([O:24][CH3:25])[CH:18]=2)[C:9]2=[N:10][CH:11]=[C:12]([I:14])[CH:13]=[C:8]2[N:7]=1)[CH3:2].[OH-].[Na+].Cl[CH2:30][C:31]1[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[N:35][CH:36]=1>CN(C)C=O.O1CCCC1.[Cl-].[Na+].O>[CH2:1]([O:3][C:4](=[O:26])[NH:5][C:6]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:30][C:31]3[CH:36]=[N:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)=[C:19]([O:24][CH3:25])[CH:18]=2)[C:9]2=[N:10][CH:11]=[C:12]([I:14])[CH:13]=[C:8]2[N:7]=1)[CH3:2]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 137528915-(Chloromethyl)-2-methoxypyridineHCID 131733016ethyl (3-(4-hydroxy-3-methoxybenzyl)-6-iodo-3H-imidazo[4,5-b]pyridin-2-yl)carbamate

Product 1

HCID 131733017ethyl (6-iodo-3-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-3H-imidazo[4,5-b]pyridin-2-yl)carbamateYield 71%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of ethyl(3-(4-hydroxy-3-methoxybenzyl)-6-iodo-3H-imidazo[4,5-b]pyridin-2-yl)carbamate ( ) (1.30 g, 2.78 mmol) and 5M aqueous sodium hydroxide solution (0.8 mL, 4.00 mmol) in N,N-dimethylformamide (10 mL) and tetrahydrofuran (10 mL) was added 5-(chloromethyl)-2-methoxypyridine (0.567 g, 3.60 mmol). The resulting mixture was allowed to stir at room temperature. After 2 h, the mixture was diluted with brine (40 mL) and extracted with ethyl acetate (3×40 mL). The combined organic phases were dried over sodium sulfate, filtered, and concentrated to provide 1.10 g (71%) of ethyl(6-iodo-3-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-3H-imidazo[4,5-b]pyridin-2-yl)carbamate as a white solid.

Workup

  1. extractionextracted with ethyl acetate (3×40 mL)
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-825ba5298f1345bb84c3c4f2890090f6
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

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