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

HRID 929185노트

반응식

HRID 929185 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-eb3553aff22944769b1a5a93a9f7ebbf
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290517B2

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