Ammonium Chloride → tert-butyl N-(3-bromo-2,6-dimethylpyrazolo[5,1-b][1,3]thiazol-7-yl)carbamate

HRID 41261

反応式

HRID 41261 の反応式
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[C:9]([CH3:17])=[N:10][N:11]2[CH:15]=[C:14]([CH3:16])[S:13][C:12]=12)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[Br:24]C(F)(F)C(F)(F)Br.[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[C:9]([CH3:17])=[N:10][N:11]2[C:15]([Br:24])=[C:14]([CH3:16])[S:13][C:12]=12)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 313011,2-Dibromo-1,1,2,2-tetrafluoroethaneHCID 58223486tert-butyl N-(2,6-dimethylpyrazolo[5,1-b][1,3]thiazol-7-yl)carbamateHCID 178418339Butyllithium

生成物 1

HCID 58223468tert-butyl N-(3-bromo-2,6-dimethylpyrazolo[5,1-b][1,3]thiazol-7-yl)carbamate収率 58.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A tetrahydrofuran (10 mL) solution of tert-butyl(2,6-dimethylpyrazolo[5,1-b][1,3]thiazol-7-yl)carbamate (266 mg, 0.995 mmol) was cooled to −78° C., and n-butyllithium (2.64M, 0.829 mL, 2.19 mmol) was added dropwise and the mixture was stirred for 10 minutes. Then, 1,2-dibromotetrafluoroethane (0.142 ml, 1.19 mmol) was added to the mixture, and the reaction mixture was warmed to room temperature and stirred at room temperature over one day and night. To the reaction mixture, a saturated aqueous solution of ammonium chloride was added, and a substance of interest was extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by medium pressure silica gel column chromatography (n-heptane/ethyl acetate: 3/1 then 2/1) to obtain the title compound (203 mg, 0.586 mmol).

後処理

  1. stirringstirred at room temperature over one day and night
  2. extractiona substance of interest was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by medium pressure silica gel column chromatography (n-heptane/ethyl acetate

出典と根拠

ORDレコード
ord-eabec0c259374d63b5b3aa99f9108ff7
出典データセット
uspto-grants-2013_09
特許番号
US08530504B2

関連ノート

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