Sodium Hydroxide → HCID 131733019, compound

HRID 706494Notes

Reaction equation

HRID 706494 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+].CC1C=CC(S(O[CH2:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]([F:53])([F:52])[C:48]([F:51])([F:50])[F:49])=[CH:43][CH:42]=2)(=O)=O)=CC=1>O1CCCC1.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][CH2:40][C:41]3[CH:42]=[CH:43][C:44]([C:47]([F:52])([F:53])[C:48]([F:49])([F:50])[F:51])=[CH:45][CH:46]=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

6

Reactant 3

HCID 14798Sodium HydroxideHCID 118114175HCID 118114175, compoundHCID 131733016ethyl (3-(4-hydroxy-3-methoxybenzyl)-6-iodo-3H-imidazo[4,5-b]pyridin-2-yl)carbamate

Product 1

HCID 131733019HCID 131733019, compoundYield 25.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl(3-(4-hydroxy-3-methoxybenzyl)-6-iodo-3H-imidazo[4,5-b]pyridin-2-yl)carbamate (Example 3-36-1) (0.24 g, 0.52 mmol) in tetrahydrofuran (20 mL) was added 5M aqueous sodium hydroxide solution (0.2 mLs, 1.00 mmol). The resulting mixture was allowed to stir at room temperature. After 2 h, the mixture was concentrated, and the residue was dissolved in N,N-dimethylformamide (10 mL). The mixture was treated with 4-(perfluoroethyl)benzyl 4-methylbenzenesulfonate (0.40 g, 1.04 mmol), and the mixture was warmed to 80° C. After 3 h, the mixture was allowed to cool to room temperature and was diluted with water (20 mL). The mixture was extracted with ethyl acetate (3×40 mL), and the combined organic phases were dried over sodium sulfate, filtered, and concentrated to provide 0.090 g of ethyl(6-iodo-3-(3-methoxy-4-((4-(perfluoroethyl)benzyl)oxy)benzyl)-3H-imidazo[4,5-b]pyridin-2-yl)carbamate as a brown solid.

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionthe residue was dissolved in N,N-dimethylformamide (10 mL)
  3. temperaturethe mixture was warmed to 80° C
  4. waitAfter 3 h
  5. temperatureto cool to room temperature
  6. extractionThe mixture was extracted with ethyl acetate (3×40 mL)
  7. dry with materialthe combined organic phases were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-05f5183980d747c0b7482ac5cef49b51
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

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