Dimethylformamide → 4-Methyl-3-([5-(pyrrolidin-1-ylmethyl)pyridin-3-yl]ethynyl)benzoic acid

HRID 1527850노트

반응식

HRID 1527850 반응식
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:8]=1)#[CH:2].I[C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:19]([OH:21])=[O:20].CN(C=O)C.CCN(C(C)C)C(C)C>C(N(CC)CC)C.C(OCC)(=O)C>[CH3:25][C:24]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][C:16]=1[C:2]#[C:1][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:8]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 6216403-Iodo-4-methylbenzoic acidHCID 212559433-Ethynyl-5-(pyrrolidin-1-ylmethyl)pyridine

생성물 1

HCID 688989594-Methyl-3-([5-(pyrrolidin-1-ylmethyl)pyridin-3-yl]ethynyl)benzoic acid

시약·촉매·용매 2

HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

can be prepared in a manner similar to that described above for the Sonogashira reaction. 3-Ethynyl-5-(pyrrolidin-1-ylmethyl)pyridine and 3-iodo-4-methylbenzoic acid are used as coupling partners. Alternatively, the solvent (DMF) can be replaced by ethyl acetate and the base (Hunig base) can be replaced by triethylamine. The product can be isolated by filtration of the crude reaction mixture. The filter cake is washed sequentially with a solvent such as ethyl acetate and then water, then dried in a vacuum oven. Further purification can be achieved by slurrying the solids in water adjusted to pH 3 with the addition of concentrated HCl. After filtration and water wash, the product can be dried in a vacuum oven.

후처리

  1. customcan be prepared in a manner similar to
  2. customthat described above for the Sonogashira reaction
  3. customThe product can be isolated by filtration of the crude
  4. customreaction mixture
  5. washThe filter cake is washed sequentially with a solvent such as ethyl acetate
  6. dry with materialwater, then dried in a vacuum oven
  7. customFurther purification
  8. additionadjusted to pH 3 with the addition of concentrated HCl
  9. filtrationAfter filtration and water
  10. washwash
  11. customthe product can be dried in a vacuum oven

출처 및 근거

ORD 기록
ord-a8608c670674492e86d00137db063ae0
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090561B2

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