Cyclopropanemethanol → 6-(4-Fluoro-phenyl)-5-cyclopropylmethoxy-pyrazine-2-carboxylic acid

HRID 639346노트

반응식

HRID 639346 반응식
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.CC(C)([O-])C.[K+].C[O:13][C:14]([C:16]1[CH:21]=[N:20][C:19](Br)=[C:18]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[N:17]=1)=[O:15]>O1CCCC1>[F:29][C:26]1[CH:25]=[CH:24][C:23]([C:18]2[N:17]=[C:16]([C:14]([OH:15])=[O:13])[CH:21]=[N:20][C:19]=2[O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[CH:28][CH:27]=1

참가 물질

5

반응물 3

HCID 75644CyclopropanemethanolHCID 23665647Potassium tert-butoxideHCID 866169575-Bromo-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acid methyl ester

생성물 1

HCID 675047836-(4-Fluoro-phenyl)-5-cyclopropylmethoxy-pyrazine-2-carboxylic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Cyclopropyl-methanol (2.2 g, 30.6 mmol, 10.0 eq) was dissolved in dry tetrahydrofuran (10 ml, 20 vol) and potassium tert-butoxide (3.4 g, 30.6 mmol, 10.0 eq) added portion-wise. After stirring for 15 minutes at room temperature 5-bromo-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acid methyl ester (0.95 g, 3.06 mmol, 1.0 eq) was added drop-wise as a tetrahydrofuran (10 ml) solution. The reaction mixture was stirred overnight at room temperature or until deemed complete by HPLC-MS analysis. The solution was concentrated in vacuo and the residue re-dissolved in ethyl acetate (20 ml). The resulting solution was washed with water (5 ml) and the aqueous phase extracted with ethyl acetate (10 ml). The combined organic phases were dried over magnesium sulphate, filtered and concentrated in vacuo to afford 6-(4-fluoro-phenyl)-5-cyclopropylmethoxy-pyrazine-2-carboxylic acid. Yield=0.89 g (75%).

후처리

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue re-dissolved in ethyl acetate (20 ml)
  3. washThe resulting solution was washed with water (5 ml)
  4. extractionthe aqueous phase extracted with ethyl acetate (10 ml)
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7d7136ad268a4ef39163d7a29ce897a4
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691863B2

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