Trifluoroacetic acid → [5-Fluoro-3-(4-phenylsulfonylpyridin-3-ylmethyl)-2-methylindol-1-yl]acetic acid methyl ester

HRID 1944432

反応式

HRID 1944432 の反応式
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[C:15]1([S:21]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][C:25]=2[CH:30]=O)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:32][O:33][C:34](=[O:47])[CH2:35][N:36]1[C:44]2[C:39](=[CH:40][C:41]([F:45])=[CH:42][CH:43]=2)[CH:38]=[C:37]1[CH3:46]>ClCCl.ClCCCl>[CH3:32][O:33][C:34](=[O:47])[CH2:35][N:36]1[C:44]2[C:39](=[CH:40][C:41]([F:45])=[CH:42][CH:43]=2)[C:38]([CH2:30][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][C:24]=2[S:21]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:22])=[O:23])=[C:37]1[CH3:46]

参加物

7

反応物 4

HCID 6422Trifluoroacetic acid2 回HCID 12052Triethylsilane2 回HCID 58247161Methyl 2-(5-fluoro-2-methyl-1H-indol-1-yl)acetateHCID 866521924-Phenylsulfonylpyridine-3-carbaldehyde

生成物 1

HCID 67044979[5-Fluoro-3-(4-phenylsulfonylpyridin-3-ylmethyl)-2-methylindol-1-yl]acetic acid methyl ester収率 14.1%

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 (5.1 g), trifluoroacetic acid (3.1 g) and 1,2-dichloroethane (20 mL) at −10° C. was treated dropwise with a mixture of 4-phenylsulfonylpyridine-3-carbaldehyde (1.9 g), (5-fluoro-2-methylindol-1-yl)acetic acid methyl ester (0.66 g) and 1,2-dichloroethane (20 mL), and the resulting mixture was stirred at room temperature for 20 hours. The mixture was treated with additional triethylsilane (5.1 g) and trifluoroacetic acid (3.1 g), and stirred at room temperature for 3 hours and then at 50° C. for 20 hours. The mixture was diluted with dichloromethane, washed with saturated aqueous sodium hydrogen carbonate solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (1:0 to 0:1 by volume), followed by trituration with diethyl ether to afford the title compound as a yellow powder (0.19 g).

後処理

  1. stirringstirred at room temperature for 3 hours
  2. waitat 50° C. for 20 hours
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over magnesium sulfate
  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 cyclohexane and ethyl acetate (1:0 to 0:1 by volume)

出典と根拠

ORDレコード
ord-1baa32d7125a4cff83924cac7c8e3533
出典データセット
uspto-grants-2013_03
特許番号
US08394836B2

関連ノート

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