Ethyl Acetate → 6-chloro-2-(methylsulfonyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridine

HRID 929185Notes

Reaction equation

HRID 929185 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[NH:8][C:9]([S:11]([CH3:14])(=[O:13])=[O:12])=[N:10][C:4]=2[CH:3]=1.C(N(CC)C(C)C)(C)C.[CH3:24][Si:25]([CH3:32])([CH3:31])[CH2:26][CH2:27][O:28][CH2:29]Cl.CCOC(C)=O>CN(C=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[N:8]([CH2:29][O:28][CH2:27][CH2:26][Si:25]([CH3:32])([CH3:31])[CH3:24])[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])=[N:10][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 900420736-chloro-2-(methylsulfonyl)-3H-imidazo[4,5-c]pyridine

Product 1

HCID 900421456-chloro-2-(methylsulfonyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 6-chloro-2-(methylsulfonyl)-3H-imidazo[4,5-c]pyridine (847 mg, 3.66 mmol) and N,N-diisopropylethylamine (5.11 mL, 29.20 mmol) in anhydrous DMF (25.0 mL) was added 2-(trimethylsilyl)ethoxymethyl chloride (3.24 mL, 18.28 mmol). The reaction was stirred under N2 at RT for 18 h, then added to EtOAc (1.4 L) and washed with saturated NH4Cl (0.3 L). The aqueous layer was separated and back-extracted with EtOAc (0.3 L). The combined organic layers were evaporated under reduced pressure. Flash chromatography of the resulting residue utilizing a 40 g silica RediSep Rf® Gold column and employing a 0-30% EtOAc/hexane gradient afforded the title compound. LC-MS: calculated for C13H20ClN3O3SSi 361.07 observed m/e: 362.31 (M+H)+ (Rt 1.32/2.0 min)

Workup

  1. washwashed with saturated NH4Cl (0.3 L)
  2. customThe aqueous layer was separated
  3. extractionback-extracted with EtOAc (0.3 L)
  4. customThe combined organic layers were evaporated under reduced pressure

Sources & evidence

ORD record
ord-eb3553aff22944769b1a5a93a9f7ebbf
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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