Water → HCID 178504257, compound

HRID 929157Notes

Reaction equation

HRID 929157 reaction equation
[S-2].[Na+].[Na+].[C:4]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]3[N:16]=[C:17]([S:27](C)(=O)=O)[N:18]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:13]3=[CH:12][C:11]=2[Cl:31])=[CH:6][CH:5]=1.O>CN(C=O)C>[C:4]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:5]=[CH:6][C:7]([C:10]2[N:15]=[C:14]3[N:16]=[C:17]([SH:27])[N:18]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:13]3=[CH:12][C:11]=2[Cl:31])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14804Sodium SulfideHCID 682826082-[[6-Chloro-2-methylsulfonyl-5-(4-phenylphenyl)imidazo[4,5-b]pyridin-1-yl]methoxy]ethyl-trimethyl-silane

Product 1

HCID 178504257HCID 178504257, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium sulfide (65.6 mg, 0.840 mmol) was added to a stirred mixture of 5-([1,1′-biphenyl]-4-yl)-6-chloro-2-(methylsulfonyl)-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-imidazo[4,5-b]pyridine (144 mg, 0.280 mmol) in DMF (2 ml) and the mixture was stirred at room temperature for 3 h. Water (30 mL) was added and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic fractions were washed with brine (saturated, 30 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel Biotage™ 25S, eluting with 0-30% EtOAc/hexane to give title compound. LC-MS: calculated for C24H26ClN3OSSi 467.13 observed m/e: 468.12 (M+H)+ (Rt 1.38/2 min).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×30 mL)
  2. washThe combined organic fractions were washed with brine (saturated, 30 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by column chromatography on silica gel Biotage™ 25S
  7. washeluting with 0-30% EtOAc/hexane

Sources & evidence

ORD record
ord-ef2da9babdda4525892ab5c2c437965a
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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