Trifluoroacetic acid → [3-(5-benzenesulfonyl-1-methyl-1H-imidazol-4-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester

HRID 1944497ノート

反応式

HRID 1944497 の反応式
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[CH3:15][O:16][C:17](=[O:30])[CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=2)[CH:21]=[C:20]1[CH3:29].[C:31]1([S:37]([C:40]2[N:44]([CH3:45])[CH:43]=[N:42][C:41]=2[CH:46]=O)(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>ClCCl.ClCCCl>[CH3:15][O:16][C:17](=[O:30])[CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=2)[C:21]([CH2:46][C:41]2[N:42]=[CH:43][N:44]([CH3:45])[C:40]=2[S:37]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)(=[O:38])=[O:39])=[C:20]1[CH3:29]

参加物

7

反応物 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58247161Methyl 2-(5-fluoro-2-methyl-1H-indol-1-yl)acetateHCID 866522145-benzenesulfonyl-1-methyl-1H-imidazole-4-carbaldehyde

生成物 1

HCID 67045042[3-(5-benzenesulfonyl-1-methyl-1H-imidazol-4-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester収率 59.6%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

A mixture of triethylsilane (0.17 g), trifluoroacetic acid (0.10 g) and 1,2-dichloroethane (5.0 mL) at −5° C. was treated dropwise with a mixture of (5-fluoro-2-methylindol-1-yl)acetic acid methyl ester (0.022 g), 5-benzenesulfonyl-1-methyl-1H-imidazole-4-carbaldehyde (0.030 g) and 1,2-dichloroethane (3.0 mL), and the resulting mixture was stirred at room temperature overnight and then at 45° C. for 2 hours. The mixture was diluted with dichloromethane, washed with saturated aqueous sodium hydrogen carbonate solution and dried using a phase separation cartridge. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and dichloromethane (0:1 to 2:5 by volume) to afford the title compound as a yellow oil (0.027 g).

後処理

  1. waitat 45° C. for 2 hours
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution
  3. customdried
  4. customa phase separation cartridge
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel
  7. washeluting with a mixture of ethyl acetate and dichloromethane (0:1 to 2:5 by volume)

出典と根拠

ORDレコード
ord-a345620d4f9a4c3e89efeda8a03ab657
出典データセット
uspto-grants-2013_03
特許番号
US08394836B2

反応ノート

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