Hexane → tert-butyl N-(7-bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethylcarbamate

HRID 347874노트

반응식

HRID 347874 반응식
C([Li])CCC.CCCCCC.[CH:12]1([CH2:15][N:16]([C:24]2[C:25]([CH2:33][CH3:34])=[N:26][N:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=23)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:14][CH2:13]1.[Br:35]C(F)(F)C(F)(F)Br.C(=O)(O)[O-].[Na+]>O1CCCC1>[Br:35][C:32]1[N:27]2[N:26]=[C:25]([CH2:33][CH3:34])[C:24]([N:16]([CH2:15][CH:12]3[CH2:13][CH2:14]3)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[C:28]2[CH:29]=[CH:30][CH:31]=1

참가 물질

7

반응물 5

HCID 8058HexaneHCID 313011,2-Dibromo-1,1,2,2-tetrafluoroethaneHCID 516892Sodium BicarbonateHCID 21084192tert-butyl N-cyclopropylmethyl-N-(2-ethylpyrazolo[1,5-a]pyridin-3-yl)carbamateHCID 178418339Butyllithium

생성물 1

HCID 21084186tert-butyl N-(7-bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethylcarbamate수율 87.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of n-butyllithium in hexane (1.6M, 3.88 mL, 6.18 mmol) was added dropwise to a solution of tert-butyl N-cyclopropylmethyl-N-(2-ethylpyrazolo[1,5-a]pyridin-3-yl)carbamate (1.5 g, 4.76 mmol) in tetrahydrofuran (15 mL) at −70° C. After stirring the reaction mixture for 50 minutes at the same temperature, 1,2-dibromotetrafluoroethane (1.0 mL, 8.33 mmol) was added dropwise to the reaction mixture. The temperature of the reaction mixture was slowly increased and aqueous sodium bicarbonate was added at 0° C. The reaction mixture was extracted with ethyl acetate, and the organic extract was washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to afford 1.65 g of the title compound as a yellow oil (87.8% yield).

후처리

  1. additionwas added dropwise to the reaction mixture
  2. temperatureThe temperature of the reaction mixture was slowly increased
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. extractionthe organic extract
  5. washwas washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)

출처 및 근거

ORD 기록
ord-394f655c183e413bb54690dd5f0ef94d
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176216B2

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