Tetrabutylammonium Fluoride → HCID 59437290、化合物

HRID 244482ノート

反応式

HRID 244482 の反応式
[Si]([O:8][CH2:9][C:10]1[S:11][CH:12]=[C:13]([C:15]([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[N:26]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[N:25]=[CH:24]3)([OH:20])[C:16]([F:19])([F:18])[F:17])[N:14]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:18][C:16]([F:17])([F:19])[C:15]([C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)[N:25]=[CH:24]2)([C:13]1[N:14]=[C:10]([CH2:9][OH:8])[S:11][CH:12]=1)[OH:20]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 594372131-[2-(tert-butyldimethylsilanyloxymethyl)thiazol-4-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol

生成物 1

HCID 59437290HCID 59437290、化合物収率 97.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a chilled (0° C.) solution of 1-[2-(tert-butyldimethylsilanyloxymethyl)thiazol-4-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol (300 mg, 0.558 mmol) in 15 mL of THF was added tetra-n-butylammonium fluoride (0.670 mL, 1 M solution in THF, 0.67 mmol). The mixture was warmed to room temperature. After 30 minutes, the mixture was quenched with 50 mL of saturated aqueous sodium bicarbonate and extracted with three 50 mL portions of diethyl ether. The combined organic layers were washed with 20 mL of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on SiO2 (0-50% ethyl acetate in hexanes) to afford 230 mg (97%) of the title compound. MS m/z 424.71 (MH+).

後処理

  1. customthe mixture was quenched with 50 mL of saturated aqueous sodium bicarbonate
  2. extractionextracted with three 50 mL portions of diethyl ether
  3. washThe combined organic layers were washed with 20 mL of brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on SiO2 (0-50% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-4196d786bad54f7a9d782c1dc2cd07a6
出典データセット
uspto-grants-2014_02
特許番号
US08658637B2

反応ノート

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