Sodium Bicarbonate → N-(2-amino-5-(pyridin-3-yl)phenyl)pyrrolidine-1-carboxamide

HRID 2201707노트

반응식

HRID 2201707 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][C:3]=1[NH:9][C:10]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19](B(O)O)[CH:18]=1.C(=O)(O)[O-].[Na+]>C1COCC1.O.[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:19]2[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=2)=[CH:4][C:3]=1[NH:9][C:10]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11]

참가 물질

7

반응물 3

HCID 516892Sodium BicarbonateHCID 27343783-Pyridinylboronic acidHCID 86712537N-(2-amino-5-bromophenyl)pyrrolidine-1-carboxamide

생성물 1

HCID 71466381N-(2-amino-5-(pyridin-3-yl)phenyl)pyrrolidine-1-carboxamide수율 68.9%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
90 °C

실험 절차

To a solution of N-(2-amino-5-bromophenyl)pyrrolidine-1-carboxamide (0.26 g, 0.72 mmol) in THF (10 mL) and water (5 mL) were added pyridin-3-ylboronic acid (0.13 g, 1.07 mmol, 1.5 equiv.), sodium bicarbonate (0.11 g, 1.07 mmol, 1.5 equiv.) and palladium(0) (0.08 g, 0.07 mmol, 0.1 equiv.). The reaction mass was stirred at 90° C. for sixteen hours. The reaction crude was filtered on a celite bed and diluted in ethyl acetate. The organic layers were washed with water and brine then dried over Na2SO4 and concentrated. The residue was purified by column chromatography on eluting ethyl acetate and hexane to allow N-(2-amino-5-(pyridin-3-yl)phenyl)pyrrolidine-1-carboxamide (0.14 g, 63% yield).

후처리

  1. customThe reaction crude
  2. filtrationwas filtered on a celite bed
  3. additiondiluted in ethyl acetate
  4. washThe organic layers were washed with water and brine
  5. dry with materialthen dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography
  8. washon eluting ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-2f7fc84e83604e9897f456091a5c05e2
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365498B2

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