Sodium hydride → methyl 2-(4-(tert-butoxycarbonylamino)-1H-indazol-1-yl)-2-(4-chlorophenyl)-4,4,4-trifluorobutanoate

HRID 1427278ノート

反応式

HRID 1427278 の反応式
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[N:14][N:15]2[CH:20]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)[C:21]([O:23][CH3:24])=[O:22])=[O:9])([CH3:6])([CH3:5])[CH3:4].FC(F)(F)S(O[CH2:38][C:39]([F:42])([F:41])[F:40])(=O)=O>C1COCC1>[C:3]([O:7][C:8]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[N:14][N:15]2[C:20]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)([CH2:38][C:39]([F:42])([F:41])[F:40])[C:21]([O:23][CH3:24])=[O:22])=[O:9])([CH3:6])([CH3:4])[CH3:5]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 70563540methyl 2-(4-(tert-butoxycarbonylamino)-1H-indazol-1-yl)-2-(4-chlorophenyl)acetate

生成物 1

HCID 70563216methyl 2-(4-(tert-butoxycarbonylamino)-1H-indazol-1-yl)-2-(4-chlorophenyl)-4,4,4-trifluorobutanoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A bottle flask was charged with NaH (580 mg, 14.4 mmol, 60% in oil) and then a solution of methyl 2-(4-(tert-butoxycarbonylamino)-1H-indazol-1-yl)-2-(4-chlorophenyl)acetate (3 g, 7.22 mmol), as described in Example 18 Step C, and 2,2,2-trifluoroethyl trifluoromethanesulfonate (3.35 g, 14.4 mmol) in THF (40 mL) at 0° C. The mixture was stirred for 30 min, quenched with saturated NH4Cl solution (10 mL), extracted with ethyl acetate. The organic layers were washed with brine (15 mL), dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (PE/EA=3:1) to afford the title compound as colorless oil. LC/MS m/z=498.1[M+H]+.

後処理

  1. customquenched with saturated NH4Cl solution (10 mL)
  2. extractionextracted with ethyl acetate
  3. washThe organic layers were washed with brine (15 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography (PE/EA=3:1)

出典と根拠

ORDレコード
ord-dd8af34aa3ba42cbb6dfda4efce7493c
出典データセット
uspto-grants-2015_01
特許番号
US08933113B2

反応ノート

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