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

HRID 929185ノート

反応式

HRID 929185 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-eb3553aff22944769b1a5a93a9f7ebbf
出典データセット
uspto-grants-2016_03
特許番号
US09290517B2

反応ノート

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