Sodium Hydroxide → HCID 131733019, compound

HRID 2178375Notes

Reaction equation

HRID 2178375 reaction equation
[OH:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([I:16])[CH:15]=[C:10]3[N:9]=[C:8]2[NH:17][C:18](=[O:22])[O:19][CH2:20][CH3:21])=[CH:4][C:3]=1[O:25][CH3:26].[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>[I:16][C:14]1[CH:15]=[C:10]2[N:9]=[C:8]([NH:17][C:18](=[O:22])[O:19][CH2:20][CH3:21])[N:7]([CH2:6][C:5]3[CH:23]=[CH:24][C:2]([O:1][CH2:40][C:41]4[CH:42]=[CH:43][C:44]([C:47]([F:52])([F:53])[C:48]([F:49])([F:50])[F:51])=[CH:45][CH:46]=4)=[C:3]([O:25][CH3:26])[CH:4]=3)[C:11]2=[N:12][CH:13]=1

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-e2ef5dda5e3440d9a53fe9f5f3e08bb9
Source dataset
uspto-grants-2015_06
Patent number
US09067914B1

Reaction notes

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